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-

HIDE SMILES / InChI

Molecular Formula	C13H22N4O3S
Molecular Weight	314.404
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

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 2,778	0.14 µM [Ki]
Histamine H2 receptor 46	Antagonist 2,778	0.19 µM [Ki]
Histamine H2 receptor 46	Antagonist 2,778

Conditions

Condition	Modality	Highest Phase	Product
Duodenal ulcer 42	Primary	Approved 8,429	ZANTAC 150
Gastric ulcer 67	Primary	Approved 8,429	ZANTAC 150
Gastroesophageal reflux disease 59	Primary	Approved 8,429	ZANTAC 150
Zollinger-Ellison syndrome 17	Primary	Approved 8,429	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

Show entries

Dose	Population	Adverse events
100 mg single, oral Highest studied dose	healthy, adult n = 136
1500 mg single, oral Overdose	unknown, children n = 517

Showing 1 to 2 of 2 entries

Previous1Next

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1,587 substrate 1,737		inhibitor 1,852 substrate 1,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT1 512 OCT2 647 OCT3 150 MATE1 306 MATE2 263 CYP3A 214 CYP1A2 1,524	OCT1 327 OCT2 355 OCT3 80 P-gp 1,537 FMO3 67 FMO1 17 CYP1A2 1,054 CYP2A6 543 CYP2C19 991 CYP2E1 667

Drug as perpetrator

Show entries

Target	Modality	Activity	Clinical evidence
CYP1A2 1,692	inhibitor 3,277	no
CYP2D6 1,891	inhibitor 3,277	no
CYP3A 298	inhibitor 3,277	no	no (co-administration study)
OCT3 150	inhibitor 3,277	weak [IC50 290 uM]
CYP3A4 1,925	inhibitor 3,277	weak

Showing 1 to 5 of 9 entries

Previous1 2Next

Drug as victim

Show entries

Target	Modality	Activity
FMO3 67	substrate 3,367	major
FMO1 17	substrate 3,367	minor
OCT2 355	substrate 3,367	minor
CYP2A6 543	substrate 3,367	no
CYP2E1 667	substrate 3,367	no

Showing 1 to 5 of 12 entries

Previous1 2 3Next

Sourcing

Sourcing

Show entries

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

Previous1Next

PubMed

Show entries

Title	Date	PubMed
Histamine H2 antagonists and the nervous system.	1985 Dec	4072863
Comparison of ranitidine and high-dose antacid in the treatment of prepyloric or duodenal ulcer. A double-blind controlled trial.	1985 Jan	3887547
Bradycardia and neurologic disorders associated with ranitidine in a child.	1985 May	3984961
Mental confusion as a side effect of ranitidine.	1986 Feb	3946668
Depression associated with ranitidine.	1986 Jul	3717435

Showing 1 to 5 of 50 entries

Previous1 2 3 4 5…10Next

Patents

Sample Use Guides

In Vivo Use Guide

150 mg twice daily (tablets or syrup)

Route of Administration: Oral

In Vitro Use Guide

10uM ranitidine partially suppresses histamine-elicited signaling in human tubular epithelial cells

Substance Class	Chemical
Record UNII	884KT10YB7
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

RANITIDINE

Official Name

English

RANITIDINE [VANDF]

Common Name

English

RANITIDINE [MI]

Common Name

English

RANITIDINE [MART.]

Common Name

English

RANITIDINE [ORANGE BOOK]

Common Name

English

Showing 1 to 5 of 10 entries

Previous1 2Next

Show entries

Classification Tree

Code System

Code

H₂-receptor antagonists

WHO-ATC

A02BA02

Gastrointestinal medicines

WHO-ESSENTIAL MEDICINES LIST

17.1

Established Pharmacologic Class

NDF-RT

N0000175784

H₂-receptor antagonists

WHO-ATC

A02BA07

Histamine Receptor Antagonists

NDF-RT

N0000000151

Showing 1 to 5 of 8 entries

Previous1 2Next

Show entries

Code System

Code

Type

Description

RXCUI

9143

PRIMARY

RxNorm

IUPHAR

1234

PRIMARY

CHEBI

8776

PRIMARY

EVMPD

SUB10258MIG

PRIMARY

DAILYMED

884KT10YB7

PRIMARY

Showing 1 to 5 of 22 entries

Previous1 2 3 4 5Next

Show entries

Related Record

Type

Details


					XC55JSP2CX

HISTAMINE H2 RECEPTOR

TARGET -> INHIBITOR


					7AJ51I17KG

RANITIDINE BISMUTH CITRATE

SALT/SOLVATE -> PARENT

Amount:


					4007E25Z4Z

OCT-3

TRANSPORTER -> INHIBITOR


					BK76465IHM

RANITIDINE HYDROCHLORIDE

SALT/SOLVATE -> PARENT

Amount:


					B46KUN2O9L

MATE-2

TRANSPORTER -> INHIBITOR

Showing 1 to 5 of 10 entries

Previous1 2Next

Show entries

Related Record

Type

Details


					TK8SB999BQ

RANITIDINE S-OXIDE

METABOLITE INACTIVE -> PARENT

Interaction Type:

MINOR


					K131L1Z4KY

RANITIDINE N-OXIDE

METABOLITE INACTIVE -> PARENT

Amount:


					L0OF19OW3L

DESMETHYLRANITIDINE

METABOLITE INACTIVE -> PARENT


					L0OF19OW3L

DESMETHYLRANITIDINE

METABOLITE INACTIVE -> PARENT

Interaction Type:

MINOR

Qualification:

URINE


					TK8SB999BQ

RANITIDINE S-OXIDE

METABOLITE INACTIVE -> PARENT

Interaction Type:

MINOR

Qualification:

URINE

Amount:

Showing 1 to 5 of 5 entries

Previous1Next

Show entries

Related Record

Type

Details


					884KT10YB7

RANITIDINE

ACTIVE MOIETY

Amount:

Showing 1 to 1 of 1 entries

Previous1Next

Name	Property Type	Amount	Parameters
Route of Elimination	PHARMACOKINETIC	MOLE PERCENT OF AMOUNT EXCRETED [30 to 70] (average) RENAL

Volume of Distribution	PHARMACOKINETIC	[0.98 to 4] Liters/Kilogram (average) CHILDREN

Biological Half-life	PHARMACOKINETIC	[1.9 to 3] hours (average) ADULTS	ELDERLY: 3 - 4 HOURS CHILDREN: 1.7 - 2.8 HOURS ADULTS, RENAL IMPAIRMENT: 4.8 - 9.8 HOURS

MAXIMUM TOLERATED DOSE	TOXICITY	400 mg/day (average)	NON-ULCER INDIGESTION, PROPHYLAXIS AND TREATMENT: 300 MG/DAY

Volume of Distribution	PHARMACOKINETIC	[1.04 to 4.09] Liters/Kilogram (average) ADULTS

PROTEIN BINDING	PHARMACOKINETIC	15 % (average)

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator