Betaxolol: Difference between revisions

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{{Infobox drug
{{Infobox drug
| verifiedrevid = 459977756
| verifiedrevid = 459977756
| IUPAC_name = (''RS'')-1-{4-[2-(cyclopropylmethoxy)ethyl]-<br/>phenoxy}-3-(isopropylamino)propan-2-ol
| image = Betaxolol structure.svg
| image = Betaxolol structure.svg
| chirality = [[Racemic mixture]]
| width = 250px
| image2 = Betaxolol ball-and-stick.png
| image2 = Betaxolol ball-and-stick.png
| width = 250px
| width2 =  


<!--Clinical data-->
<!-- Clinical data -->
| tradename = Kerlone
| tradename = Kerlone
| Drugs.com = {{drugs.com|monograph|betaxolol-hydrochloride}}
| Drugs.com = {{drugs.com|monograph|betaxolol-hydrochloride}}
Line 17: Line 16:
| legal_status = Rx-only
| legal_status = Rx-only
| routes_of_administration = [[Oral administration|By mouth]], [[human eye|ocular]]
| routes_of_administration = [[Oral administration|By mouth]], [[human eye|ocular]]
| class = [[Beta blocker]]; [[β-Adrenergic receptor]] [[receptor antagonist|antagonist]]; [[Binding selectivity|Selective]] [[beta-1 adrenergic receptor|β<sub>1</sub>-adrenergic receptor]] [[receptor antagonist|antagonist]]
| ATC_prefix = C07
| ATC_suffix = AB05
| ATC_supplemental = {{ATC|S01|ED02}}


<!--Pharmacokinetic data-->
<!-- Pharmacokinetic data -->
| bioavailability = 89%
| bioavailability = 89%
| protein_bound =
| metabolism = [[Liver]]
| metabolism = [[Liver]]
| metabolites =
| elimination_half-life = 14–22 hours
| elimination_half-life = 14–22 hours
| excretion = [[Kidney]] (20%)
| excretion = [[Kidney]] (20%)


<!--Identifiers-->
<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 63659-18-7
| CAS_number = 63659-18-7
| ATC_prefix = C07
| ATC_suffix = AB05
| ATC_supplemental = {{ATC|S01|ED02}}
| PubChem = 2369
| PubChem = 2369
| IUPHAR_ligand = 549
| IUPHAR_ligand = 549
Line 44: Line 46:
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 423
| ChEMBL = 423
| synonyms =


<!--Chemical data-->
<!-- Chemical data -->
| IUPAC_name = (''RS'')-1-{4-[2-(cyclopropylmethoxy)ethyl]-<br/>phenoxy}-3-(isopropylamino)propan-2-ol
| C=18 | H=29 | N=1 | O=3
| C=18 | H=29 | N=1 | O=3
| chirality = [[Racemic mixture]]
| SMILES = O(CCc1ccc(OCC(O)CNC(C)C)cc1)CC2CC2
| SMILES = O(CCc1ccc(OCC(O)CNC(C)C)cc1)CC2CC2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
Line 54: Line 59:
}}
}}
<!-- Definition and medical uses -->
<!-- Definition and medical uses -->
'''Betaxolol''' is a selective [[beta blocker|beta<sub>1</sub> receptor blocker]] used in the treatment of [[hypertension]] and [[angina]].<ref>{{cite journal | vauthors = Buckley MM, Goa KL, Clissold SP | title = Ocular betaxolol. A review of its pharmacological properties, and therapeutic efficacy in glaucoma and ocular hypertension | journal = Drugs | volume = 40 | issue = 1 | pages = 75–90 | date = July 1990 | pmid = 2202584 | doi = 10.2165/00003495-199040010-00005 | s2cid = 46962082 }}</ref> It is also a [[Adrenergic antagonist|adrenergic]] blocker with no partial agonist action and minimal membrane stabilizing activity.<ref>{{Cite web |title=Google Scholar |url=https://scholar.google.com/scholar?q=%22Betaxolol%22#d=gs_qabs&t=1703552255390&u=#p=8zHRlC92iIoJ |access-date=2023-12-26 |website=scholar.google.com}}</ref> Being selective for beta<sub>1</sub> receptors, it typically has fewer systemic [[adverse drug reaction|side effect]]s than non-selective beta-blockers, for example, not causing [[bronchospasm]] (mediated by beta<sub>2</sub> receptors) as [[timolol]] may. Betaxolol also shows greater affinity for beta<sub>1</sub> receptors than [[metoprolol]]. In addition to its effect on the heart, betaxolol reduces the pressure within the eye ([[intraocular pressure]]). This effect is thought to be caused by reducing the production of the liquid (which is called the [[aqueous humor]]) within the eye. The precise mechanism of this effect is not known. The reduction in intraocular pressure reduces the risk of damage to the [[optic nerve]] and loss of vision in patients with elevated intraocular pressure due to [[glaucoma]].  
'''Betaxolol''' is a [[beta blocker]] used in the treatment of [[hypertension]] and [[angina]].<ref>{{cite journal | vauthors = Buckley MM, Goa KL, Clissold SP | title = Ocular betaxolol. A review of its pharmacological properties, and therapeutic efficacy in glaucoma and ocular hypertension | journal = Drugs | volume = 40 | issue = 1 | pages = 75–90 | date = July 1990 | pmid = 2202584 | doi = 10.2165/00003495-199040010-00005 | s2cid = 46962082 }}</ref>
 
<!-- Side effects and mechanism of action -->
It acts as a [[binding selectivity|selective]] [[beta-1 adrenergic receptor|β<sub>1</sub>-adrenergic receptor]] [[receptor antagonist|antagonist]].


<!-- Society and culture -->
<!-- Society and culture -->
It was patented in 1975 and approved for medical use in 1983.<ref>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=461 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA461 |language=en}}</ref>
The drug was patented in 1975 and approved for medical use in 1983.<ref>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=461 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA461 |language=en}}</ref>


==Medical uses==
==Medical uses==
 
===Hypertension===
=== Hypertension ===
Betaxolol is most commonly ingested orally alone or with other medications for the management of [[essential hypertension]].<ref>{{cite book | vauthors = Tajran J, Goyal A | chapter = Betaxolol |date=2023 |chapter-url=http://www.ncbi.nlm.nih.gov/books/NBK557870/ | title = StatPearls |access-date=2023-12-26 |place=Treasure Island (FL) |publisher=StatPearls Publishing |pmid=32491793 }}</ref> It is a cardioselective beta blocker, targeting beta-1 adrenergic receptors found in the cardiac muscle. Blood pressure is decreased by the mechanism of blood vessels relaxing and improving the flow of blood.<ref>{{Cite web |title=Betaxolol | work = MedlinePlus Drug Information |url=https://medlineplus.gov/druginfo/meds/a609023.html |access-date=2023-01-12 | publisher = U.S. National Library of Medicine |language=en}}</ref><ref>{{Cite web |title=Betaxolol: MedlinePlus Drug Information |url=https://medlineplus.gov/druginfo/meds/a609023.html |access-date=2023-12-26 |website=medlineplus.gov |language=en}}</ref>
Betaxolol is most commonly ingested orally alone or with other medications for the management of [[essential hypertension]].<ref>{{cite book | vauthors = Tajran J, Goyal A | chapter = Betaxolol |date=2023 |chapter-url=http://www.ncbi.nlm.nih.gov/books/NBK557870/ | title = StatPearls |access-date=2023-12-26 |place=Treasure Island (FL) |publisher=StatPearls Publishing |pmid=32491793 }}</ref> It is a cardioselective beta blocker, targeting beta-1 adrenergic receptors found in the cardiac muscle. Blood pressure is decreased by the mechanism of blood vessels relaxing and improving the flow of blood.<ref>{{Cite web |title=Betaxolol | work = MedlinePlus Drug Information |url=https://medlineplus.gov/druginfo/meds/a609023.html |access-date=2023-01-12 | publisher = U.S. National Library of Medicine |language=en}}</ref><ref>{{Cite web |title=Betaxolol: MedlinePlus Drug Information |url=https://medlineplus.gov/druginfo/meds/a609023.html |access-date=2023-12-26 |website=medlineplus.gov |language=en}}</ref>


=== Glaucoma ===
===Glaucoma===
Ophthalmic betaxolol is an available treatment for [[primary open angle glaucoma]] (POAG) and optical hypertension. Betaxolol effectively prevents the increase of intracellular calcium, which leads to increased production of the aqueous humor. In the context of open angle glaucoma, increased aqueous humor produced by ciliary bodies increases intraocular pressure, causing degeneration of [[retinal ganglion cell]]s and the optic nerve.<ref name = "Tajran_2022">{{cite book | vauthors = Tajran J, Goyal A | chapter = Betaxolol |date=2022 | chapter-url= http://www.ncbi.nlm.nih.gov/books/NBK557870/ | title = StatPearls |place=Treasure Island (FL) |publisher=StatPearls Publishing |pmid=32491793 |access-date=2023-01-12 }}</ref>
Ophthalmic betaxolol is an available treatment for [[primary open angle glaucoma]] (POAG) and optical hypertension. Betaxolol effectively prevents the increase of intracellular calcium, which leads to increased production of the aqueous humor. In the context of open angle glaucoma, increased aqueous humor produced by ciliary bodies increases intraocular pressure, causing degeneration of [[retinal ganglion cell]]s and the optic nerve.<ref name = "Tajran_2022">{{cite book | vauthors = Tajran J, Goyal A | chapter = Betaxolol |date=2022 | chapter-url= http://www.ncbi.nlm.nih.gov/books/NBK557870/ | title = StatPearls |place=Treasure Island (FL) |publisher=StatPearls Publishing |pmid=32491793 |access-date=2023-01-12 }}</ref>


Furthermore, betaxolol is additionally able to protect retinal neurones following topical application from [[excitotoxicity]] or [[Ischemia-reperfusion injury|ischemia-reperfusion]], providing a neuroprotective effect. This is thought to be attributed to its capacity to attenuate neuronal calcium and sodium influx.<ref>{{cite journal | vauthors = Wood JP, Schmidt KG, Melena J, Chidlow G, Allmeier H, Osborne NN | title = The beta-adrenoceptor antagonists metipranolol and timolol are retinal neuroprotectants: comparison with betaxolol | journal = Experimental Eye Research | volume = 76 | issue = 4 | pages = 505–516 | date = April 2003 | pmid = 12634114 | doi = 10.1016/s0014-4835(02)00335-4 }}</ref> Betaxolol is also an effective treatment for [[Intraocular pressure]]<ref>{{cite journal | vauthors = Goldberg I, Goldberg H | title = Betaxolol eye drops. A clinical trial of safety and efficacy | journal = Australian and New Zealand Journal of Ophthalmology | volume = 23 | issue = 1 | pages = 17–24 | date = February 1995 | pmid = 7619450 | doi = 10.1111/j.1442-9071.1995.tb01640.x }}</ref><br>
Furthermore, betaxolol is additionally able to protect retinal neurones following topical application from [[excitotoxicity]] or [[Ischemia-reperfusion injury|ischemia-reperfusion]], providing a neuroprotective effect. This is thought to be attributed to its capacity to attenuate neuronal calcium and sodium influx.<ref>{{cite journal | vauthors = Wood JP, Schmidt KG, Melena J, Chidlow G, Allmeier H, Osborne NN | title = The beta-adrenoceptor antagonists metipranolol and timolol are retinal neuroprotectants: comparison with betaxolol | journal = Experimental Eye Research | volume = 76 | issue = 4 | pages = 505–516 | date = April 2003 | pmid = 12634114 | doi = 10.1016/s0014-4835(02)00335-4 }}</ref> Betaxolol is also an effective treatment for [[Intraocular pressure]]<ref>{{cite journal | vauthors = Goldberg I, Goldberg H | title = Betaxolol eye drops. A clinical trial of safety and efficacy | journal = Australian and New Zealand Journal of Ophthalmology | volume = 23 | issue = 1 | pages = 17–24 | date = February 1995 | pmid = 7619450 | doi = 10.1111/j.1442-9071.1995.tb01640.x }}</ref><br>
=== Paronychia ===
 
===Other uses===
Betaxolol has been used to treat [[anxiety]] as well.<ref name="BoyceBalloneCerta2021">{{cite journal | vauthors = Boyce TG, Ballone NT, Certa KM, Becker MA | title = The Use of β-Adrenergic Receptor Antagonists in Psychiatry: A Review | journal = J Acad Consult Liaison Psychiatry | volume = 62 | issue = 4 | pages = 404–412 | date = 2021 | pmid = 34210401 | doi = 10.1016/j.jaclp.2020.12.009 | url = }}</ref><ref name="ArcherWilesKessler2025">{{cite journal | vauthors = Archer C, Wiles N, Kessler D, Turner K, Caldwell DM | title = Beta-blockers for the treatment of anxiety disorders: A systematic review and meta-analysis | journal = J Affect Disord | volume = 368 | issue = | pages = 90–99 | date = January 2025 | pmid = 39271062 | doi = 10.1016/j.jad.2024.09.068 | url = }}</ref>
 
One study showed that topical betaxolol can be used in treating relapsed [[paronychia]].<ref>{{cite journal | vauthors = Yen CF, Hsu CK, Lu CW | title = Topical betaxolol for treating relapsing paronychia with pyogenic granuloma-like lesions induced by epidermal growth factor receptor inhibitors | journal = Journal of the American Academy of Dermatology | volume = 78 | issue = 6 | pages = e143–e144 | date = June 2018 | pmid = 29339238 | doi = 10.1016/j.jaad.2018.01.015 | s2cid = 39861588 }}</ref>
One study showed that topical betaxolol can be used in treating relapsed [[paronychia]].<ref>{{cite journal | vauthors = Yen CF, Hsu CK, Lu CW | title = Topical betaxolol for treating relapsing paronychia with pyogenic granuloma-like lesions induced by epidermal growth factor receptor inhibitors | journal = Journal of the American Academy of Dermatology | volume = 78 | issue = 6 | pages = e143–e144 | date = June 2018 | pmid = 29339238 | doi = 10.1016/j.jaad.2018.01.015 | s2cid = 39861588 }}</ref>


Line 75: Line 85:
* Patients with [[sinus bradycardia]], heart block greater than first degree, cardiogenic shock, and overt cardiac failure
* Patients with [[sinus bradycardia]], heart block greater than first degree, cardiogenic shock, and overt cardiac failure


== Side effects ==
==Side effects==
{{Expand section|date=January 2019}}
The adverse [[side effect]]s of betaxolol can be categorized into local and systemic effects.<ref name = "Tajran_2022" /> The local effects include:
The adverse side-effects of betaxolol can be categorized into local and systemic effects.<ref name = "Tajran_2022" /> The local effects include:


* transient irritation (20-40% of patients)
* transient irritation (20-40% of patients)
Line 103: Line 112:


{{See also|Beta blocker}}
{{See also|Beta blocker}}
==Pharmacology==
===Pharmacodynamics===
Betaxolol is a [[beta blocker]] and acts specifically as a [[binding selectivity|selective]] [[beta-1 adrenergic receptor|β<sub>1</sub>-adrenergic receptor]] [[receptor antagonist|antagonist]]. It has no [[partial agonist]] action (i.e., [[intrinsic sympathomimetic activity]]) and shows minimal [[membrane-stabilizing activity]] (i.e., [[sodium channel blockade]] or [[local anesthetic]] activity).<ref>{{Cite web |title=Google Scholar |url=https://scholar.google.com/scholar?q=%22Betaxolol%22#d=gs_qabs&t=1703552255390&u=#p=8zHRlC92iIoJ |access-date=2023-12-26 |website=scholar.google.com}}</ref> Being selective for beta<sub>1</sub> receptors, it typically has fewer systemic [[adverse drug reaction|side effect]]s than non-selective beta-blockers, for example, not causing [[bronchospasm]] (mediated by beta<sub>2</sub> receptors) as [[timolol]] may. Betaxolol also shows greater affinity for beta<sub>1</sub> receptors than [[metoprolol]]. In addition to its effect on the heart, betaxolol reduces the pressure within the eye ([[intraocular pressure]]). This effect is thought to be caused by reducing the production of the liquid (which is called the [[aqueous humor]]) within the eye. The precise mechanism of this effect is not known. The reduction in intraocular pressure reduces the risk of damage to the [[optic nerve]] and loss of vision in patients with elevated intraocular pressure due to [[glaucoma]].
==Chemistry==
The experimental [[log P]] of betaxolol is 2.4 to 2.81.<ref name="PubChem">https://pubchem.ncbi.nlm.nih.gov/compound/2369</ref><ref name="DrugBank">https://go.drugbank.com/drugs/DB00195</ref>


==History==
==History==
Line 108: Line 124:


==Society and culture==
==Society and culture==
===Brand names===
===Brand names===
Brand names include Betoptic, Betoptic S, Lokren, Kerlone.
Brand names include Betoptic, Betoptic S, Lokren, Kerlone.


== See also ==
==See also==
* [[Levobetaxolol]]
* [[Levobetaxolol]]
* [[Cicloprolol]]
* [[Cicloprolol]]


== References ==
==References==
{{Reflist}}
{{Reflist}}


== External links ==
==External links==
* [https://web.archive.org/web/20071020131717/http://products.sanofi-aventis.us/kerlone/kerlone.pdf Kerlone prescribing information]
* [https://web.archive.org/web/20071020131717/http://products.sanofi-aventis.us/kerlone/kerlone.pdf Kerlone prescribing information]


{{Beta blockers}}
{{Beta blockers}}
{{Antiglaucoma preparations and miotics}}
{{Antiglaucoma preparations and miotics}}
{{Anxiolytics}}
{{Adrenergic receptor modulators}}
{{Adrenergic receptor modulators}}


[[Category:Anxiolytics]]
[[Category:Beta blockers]]
[[Category:Beta blockers]]
[[Category:Cyclopropyl compounds]]
[[Category:Cyclopropyl compounds]]

Latest revision as of 22:33, 22 June 2025

Template:Short description Template:Cs1 config Template:Main other <templatestyles src="Infobox drug/styles.css"/> Script error: No such module "Infobox".Template:Template otherScript error: No such module "TemplatePar".{{Infobox drug/maintenance categoriesTemplate:Yesno | drug_name = | INN = | _drugtype =

| _has_physiological_data= | _has_gene_therapy=

| vaccine_type= | mab_type= | _number_of_combo_chemicals=Script error: No such module "ParameterCount". | _vaccine_data= | _mab_data= | _mab_vaccine_data= | _mab_other_data=182913O(CCc1ccc(OCC(O)CNC(C)C)cc1)CC2CC2Racemic mixture1S/C18H29NO3/c1-14(2)19-11-17(20)13-22-18-7-5-15(6-8-18)9-10-21-12-16-3-4-16/h5-8,14,16-17,19-20H,3-4,9-13H2,1-2H3NWIUTZDMDHAVTP-UHFFFAOYSA-NTemplate:StdinchiciteTemplate:Stdinchicite | _combo_data= | _physiological_data= | _clinical_data=Template:Drugs.coma609023 CBy mouth, ocularKerloneBeta blocker; β-Adrenergic receptor antagonist; Selective β1-adrenergic receptor antagonistC07Template:ATC | _legal_data=Rx-only

| _other_data=(RS)-1-{4-[2-(cyclopropylmethoxy)ethyl]-
phenoxy}-3-(isopropylamino)propan-2-ol

| _image_0_or_2 = Betaxolol structure.svgBetaxolol ball-and-stick.png | _image_LR =

| _datapage = Betaxolol (data page) | _vaccine_target=_type_not_vaccine | _legal_all=Rx-only | _ATC_prefix_supplemental=C07Template:ATC | _has_EMA_link = | CAS_number=63659-18-7 | PubChem=2369 | ChemSpiderID=2279 | ChEBI=3082 | ChEMBL=423 | DrugBank=DB00195 | KEGG=D07526 | _hasInChI_or_Key=yes | UNII=O0ZR1R6RZ2 | _hasJmol02 = |_hasMultipleCASnumbers = |_hasMultiplePubChemCIDs = |_hasMultipleChEBIs =

| _countSecondIDs=Script error: No such module "ParameterCount". | _countIndexlabels=Script error: No such module "ParameterCount". | _trackListSortletter= |QID = |QID2 = |Verifiedfields= |Watchedfields= |verifiedrevid=459977756}} Betaxolol is a beta blocker used in the treatment of hypertension and angina.[1]

It acts as a selective β1-adrenergic receptor antagonist.

The drug was patented in 1975 and approved for medical use in 1983.[2]

Medical uses

Hypertension

Betaxolol is most commonly ingested orally alone or with other medications for the management of essential hypertension.[3] It is a cardioselective beta blocker, targeting beta-1 adrenergic receptors found in the cardiac muscle. Blood pressure is decreased by the mechanism of blood vessels relaxing and improving the flow of blood.[4][5]

Glaucoma

Ophthalmic betaxolol is an available treatment for primary open angle glaucoma (POAG) and optical hypertension. Betaxolol effectively prevents the increase of intracellular calcium, which leads to increased production of the aqueous humor. In the context of open angle glaucoma, increased aqueous humor produced by ciliary bodies increases intraocular pressure, causing degeneration of retinal ganglion cells and the optic nerve.[6]

Furthermore, betaxolol is additionally able to protect retinal neurones following topical application from excitotoxicity or ischemia-reperfusion, providing a neuroprotective effect. This is thought to be attributed to its capacity to attenuate neuronal calcium and sodium influx.[7] Betaxolol is also an effective treatment for Intraocular pressure[8]

Other uses

Betaxolol has been used to treat anxiety as well.[9][10]

One study showed that topical betaxolol can be used in treating relapsed paronychia.[11]

Contraindications

  • Hypersensitivity to the drug
  • Patients with sinus bradycardia, heart block greater than first degree, cardiogenic shock, and overt cardiac failure

Side effects

The adverse side effects of betaxolol can be categorized into local and systemic effects.[6] The local effects include:

Systemically, patients taking betaxolol might experience:

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Pharmacology

Pharmacodynamics

Betaxolol is a beta blocker and acts specifically as a selective β1-adrenergic receptor antagonist. It has no partial agonist action (i.e., intrinsic sympathomimetic activity) and shows minimal membrane-stabilizing activity (i.e., sodium channel blockade or local anesthetic activity).[13] Being selective for beta1 receptors, it typically has fewer systemic side effects than non-selective beta-blockers, for example, not causing bronchospasm (mediated by beta2 receptors) as timolol may. Betaxolol also shows greater affinity for beta1 receptors than metoprolol. In addition to its effect on the heart, betaxolol reduces the pressure within the eye (intraocular pressure). This effect is thought to be caused by reducing the production of the liquid (which is called the aqueous humor) within the eye. The precise mechanism of this effect is not known. The reduction in intraocular pressure reduces the risk of damage to the optic nerve and loss of vision in patients with elevated intraocular pressure due to glaucoma.

Chemistry

The experimental log P of betaxolol is 2.4 to 2.81.[14][15]

History

Betaxolol was approved by the U.S. Food and Drug Administration (FDA) for ocular use as a 0.5% solution (Betoptic) in 1985 and as a 0.25% solution (Betoptic S) in 1989.

Society and culture

Brand names

Brand names include Betoptic, Betoptic S, Lokren, Kerlone.

See also

References

Template:Reflist

External links

Template:Beta blockers Script error: No such module "Navbox". Script error: No such module "navbox". Template:Adrenergic receptor modulators

  1. ↑ Script error: No such module "Citation/CS1".
  2. ↑ Script error: No such module "citation/CS1".
  3. ↑ Script error: No such module "citation/CS1".
  4. ↑ Script error: No such module "citation/CS1".
  5. ↑ Script error: No such module "citation/CS1".
  6. ↑ a b Script error: No such module "citation/CS1".
  7. ↑ Script error: No such module "Citation/CS1".
  8. ↑ Script error: No such module "Citation/CS1".
  9. ↑ Script error: No such module "Citation/CS1".
  10. ↑ Script error: No such module "Citation/CS1".
  11. ↑ Script error: No such module "Citation/CS1".
  12. ↑ Script error: No such module "Citation/CS1".
  13. ↑ Script error: No such module "citation/CS1".
  14. ↑ https://pubchem.ncbi.nlm.nih.gov/compound/2369
  15. ↑ https://go.drugbank.com/drugs/DB00195
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