RANITIDINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H22N4O3S
Molecular Weight	314.404
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

SMILES

CNC(NCCSCC1=CC=C(CN(C)C)O1)=C[N+]([O-])=O

InChI

InChIKey=VMXUWOKSQNHOCA-LCYFTJDESA-N

InChI=1S/C13H22N4O3S/c1-14-13(9-17(18)19)15-6-7-21-10-12-5-4-11(20-12)8-16(2)3/h4-5,9,14-15H,6-8,10H2,1-3H3/b13-9-

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Description

Ranitidine, a histamine H2-receptor antagonist, is now well established as a potent inhibitor of gastric acid secretion effective in the treatment and prophylaxis of gastrointestinal lesions aggravated by gastric acid secretion.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Histamine H2 receptor 46	Antagonist 2,849	0.14 µM [Ki]
Histamine H2 receptor 46	Antagonist 2,849	0.19 µM [Ki]
Histamine H2 receptor 46	Antagonist 2,849

Conditions

Condition	Modality	Highest Phase	Product
Duodenal ulcer 49	Primary	Approved 8,583	ZANTAC 150
Gastric ulcer 74	Primary	Approved 8,583	ZANTAC 150
Gastroesophageal reflux disease 68	Primary	Approved 8,583	ZANTAC 150
Zollinger-Ellison syndrome 17	Primary	Approved 8,583	ZANTAC 150

C_max

Value	Dose	Co-administered	Analyte	Population
440 ng/mL	150 mg single, oral		RANITIDINE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
948.6 ng × h/mL	80 mg single, oral		RANITIDINE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.69 h	80 mg single, oral		RANITIDINE plasma	Homo sapiens
2.5 h	150 mg single, oral		RANITIDINE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
85%	150 mg single, oral		RANITIDINE plasma	Homo sapiens

Doses

Doses

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Dose	Population	Adverse events
100 mg single, oral Highest studied dose	healthy, adult
1500 mg single, oral Overdose	unknown, children

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2,252 substrate 1,946		inhibitor 2,507 substrate 1,388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT1 620 OCT2 779 OCT3 159 MATE1 415 MATE2 267 CYP3A 227 CYP1A2 2,153	OCT1 393 OCT2 434 OCT3 92 P-gp 2,052 FMO3 77 FMO1 25 CYP1A2 1,197 CYP2A6 626 CYP2C19 1,119 CYP2E1 729

Drug as perpetrator

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Target	Modality	Activity	Clinical evidence
CYP1A2 2,333	inhibitor 4,027	no
CYP2D6 2,546	inhibitor 4,027	no
CYP3A 317	inhibitor 4,027	no	no (co-administration study)
OCT3 161	inhibitor 4,027	weak [IC50 290 uM]
CYP3A4 2,633	inhibitor 4,027	weak

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Drug as victim

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Target	Modality	Activity
FMO3 77	substrate 4,014	major
FMO1 25	substrate 4,014	minor
OCT2 434	substrate 4,014	minor
CYP2A6 626	substrate 4,014	no
CYP2E1 729	substrate 4,014	no

Showing 1 to 5 of 12 entries

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:8776	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8776
ChemicalBook	CB5480252	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5480252
MolPort	MolPort-003-666-370	https://www.molport.com/shop/molecule-link/MolPort-003-666-370
ZINC	ZINC000001530728	http://zinc15.docking.org/substances/ZINC000001530728

Showing 1 to 4 of 4 entries

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PubMed

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Title	Date	PubMed
Fatal renal and hepatic toxicity after treatment with diltiazem.	1987 Nov 14	3120959
First-degree atrioventricular block in a young duodenal ulcer patient treated with a standard oral dose of ranitidine.	1988 Jul	3177090
Reversible chorea due to ranitidine and cimetidine.	1988 Jul 16	2899203
Famotidine and ranitidine, but not cimetidine, cause severe, disabling headache.	1989 Feb	2563629
Mechanism of ranitidine associated anemia.	1989 Jun	2735342