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cimetidine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
histamine-H2-receptor antagonists, cimetidine derivatives	645	51481-61-9

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: cimetidine tagamet tametin ulcedin ulcedine ulcerex ulcerfen cimetidine hydrochloride cimetidine HCl	A histamine congener, it competitively inhibits HISTAMINE binding to HISTAMINE H2 RECEPTORS. Cimetidine has a range of pharmacological actions. It inhibits GASTRIC ACID secretion, as well as PEPSIN and GASTRIN output. Molecular weight: 252.34 Formula: C10H16N6S CLOGP: 0.38 LIPINSKI: 0 HAC: 6 HDO: 3 TPSA: 88.89 ALOGS: -3.16 ROTB: 5 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

cimetidine
tagamet
tametin
ulcedin
ulcedine
ulcerex
ulcerfen
cimetidine hydrochloride
cimetidine HCl

A histamine congener, it competitively inhibits HISTAMINE binding to HISTAMINE H2 RECEPTORS. Cimetidine has a range of pharmacological actions. It inhibits GASTRIC ACID secretion, as well as PEPSIN and GASTRIN output.

Molecular weight: 252.34
Formula: C10H16N6S
CLOGP: 0.38
LIPINSKI: 0
HAC: 6
HDO: 3
TPSA: 88.89
ALOGS: -3.16
ROTB: 5

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
0.80	g	O
0.80	g	P

ADMET properties:

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Property	Value	Reference
CL (Clearance)	8.10 mL/min/kg	Lombardo F, Berellini G, Obach RS
EoM (Fraction excreted unchanged in urine)	62 %	Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability)	60 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
S (Water solubility)	6.20 mg/mL	Benet LZ, Broccatelli F, Oprea TI
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Benet LZ, Broccatelli F, Oprea TI
t_half (Half-life)	2.20 hours	Lombardo F, Berellini G, Obach RS
MRTD (Maximum Recommended Therapeutic Daily Dose)	158.51 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution)	1.20 L/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.78 %	Lombardo F, Berellini G, Obach RS

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Approvals:

Date	Agency	Company	Orphan
Aug. 16, 1977	FDA

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Body tinea	158.30	13.74	44	15061	1841	63472076
Urine abnormality	149.54	13.74	58	15047	6961	63466956
Inhibitory drug interaction	140.36	13.74	44	15061	2805	63471112
Infection susceptibility increased	131.20	13.74	44	15061	3477	63470440
Urine leukocyte esterase positive	118.75	13.74	41	15064	3538	63470379
Glucose tolerance impaired	107.78	13.74	45	15060	6532	63467385
Poor quality sleep	97.11	13.74	60	15045	19875	63454042
Lymphocyte count decreased	94.28	13.74	69	15036	30188	63443729
Purpura	89.90	13.74	47	15058	11338	63462579
Hyperlipidaemia	85.54	13.74	55	15050	19516	63454401

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Chronic kidney disease	35.13	16.25	39	5888	41171	34909833
Renal injury	22.19	16.25	17	5910	11178	34939826
Mucosal erosion	20.38	16.25	7	5920	837	34950167
Palmar-plantar erythrodysaesthesia syndrome	18.06	16.25	18	5909	16777	34934227
Peptic ulcer	18.01	16.25	9	5918	2774	34948230
Decreased appetite	16.75	16.25	64	5863	166328	34784676

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Urine abnormality	158.78	13.37	62	17566	8157	79718603
Body tinea	157.55	13.37	43	17585	1811	79724949
Inhibitory drug interaction	128.05	13.37	45	17583	4408	79722352
Infection susceptibility increased	128.01	13.37	43	17585	3678	79723082
Urine leukocyte esterase positive	116.33	13.37	41	17587	4050	79722710
Lymphocyte count decreased	99.57	13.37	83	17545	47206	79679554
Glucose tolerance impaired	98.80	13.37	44	17584	8040	79718720
Poor quality sleep	93.93	13.37	60	17568	22662	79704098
Bone density decreased	80.61	13.37	45	17583	13302	79713458
Hyperlipidaemia	77.13	13.37	56	17572	26037	79700723

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	A02BA01	ALIMENTARY TRACT AND METABOLISM DRUGS FOR ACID RELATED DISORDERS DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) H2-receptor antagonists
ATC	A02BA51	ALIMENTARY TRACT AND METABOLISM DRUGS FOR ACID RELATED DISORDERS DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) H2-receptor antagonists
CHEBI has role	CHEBI:37961	H2 receptor antagonists
CHEBI has role	CHEBI:49201	anti-ulcer drugs
CHEBI has role	CHEBI:50183	P450 inhibitors
CHEBI has role	CHEBI:60809	adjuvants
FDA EPC	N0000175784	Histamine-2 Receptor Antagonist
FDA MoA	N0000000151	Histamine H2 Receptor Antagonists
MeSH PA	D000897	Anti-Ulcer Agents
MeSH PA	D065609	Cytochrome P-450 CYP1A2 Inhibitors

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Heartburn	indication	16331000
Upper gastrointestinal hemorrhage	indication	37372002
Duodenal ulcer disease	indication	51868009	DOID:1724
Zollinger-Ellison syndrome	indication	53132006	DOID:0050782
Multiple endocrine adenomas	indication	60549007
Indigestion	indication	162031009
Gastroesophageal reflux disease	indication	235595009	DOID:8534
Systemic mast cell disease	indication	397016004	DOID:349
Gastric ulcer	indication	397825006	DOID:10808
Upper GI Bleed Prevention	indication

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	13.83	acidic
pKa2	6.71	Basic
pKa3	0.0	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Histamine H2 receptor	GPCR	P25021	HRH2_HUMAN	ANTAGONIST	Kd	6.14	WOMBAT-PK	CHEMBL
5-hydroxytryptamine receptor 2A	GPCR	P28223	5HT2A_HUMAN		Ki	5.16	PDSP
Multidrug and toxin extrusion protein 1	Transporter	Q96FL8	S47A1_HUMAN		IC50	5.92	CHEMBL
Multidrug and toxin extrusion protein 2	Transporter	Q86VL8	S47A2_HUMAN	INHIBITOR	Ki	5.10	IUPHAR
Histamine H2 receptor	GPCR		HRH2_CAVPO		Kd	6.58	CHEMBL
Histamine H2 receptor	GPCR		HRH2_RAT	ANTAGONIST	Ki	5.90	IUPHAR

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External reference:

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ID	Source
003415	NDDF
004987	NDDF
101	MMSL
1231	IUPHAR_LIGAND_ID
152402	RXNORM
2261	MMSL
2756	PUBCHEM_CID
373541007	SNOMEDCT_US
3765	INN_ID
4018844	VANDF

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Acid Reducer	HUMAN OTC DRUG LABEL	1	30142-323	TABLET, FILM COATED	200 mg	ORAL	ANDA	16 sections
Cimetidine	HUMAN PRESCRIPTION DRUG LABEL	1	0093-8192	TABLET, FILM COATED	300 mg	ORAL	ANDA	20 sections
Cimetidine	HUMAN PRESCRIPTION DRUG LABEL	1	0093-8192	TABLET, FILM COATED	300 mg	ORAL	ANDA	20 sections
Cimetidine	HUMAN PRESCRIPTION DRUG LABEL	1	0093-8192	TABLET, FILM COATED	300 mg	ORAL	ANDA	20 sections
Cimetidine	HUMAN PRESCRIPTION DRUG LABEL	1	0093-8204	TABLET, FILM COATED	400 mg	ORAL	ANDA	20 sections
Cimetidine	HUMAN PRESCRIPTION DRUG LABEL	1	0093-8204	TABLET, FILM COATED	400 mg	ORAL	ANDA	20 sections
Cimetidine	HUMAN PRESCRIPTION DRUG LABEL	1	0093-8204	TABLET, FILM COATED	400 mg	ORAL	ANDA	20 sections
Cimetidine	HUMAN PRESCRIPTION DRUG LABEL	1	0093-8305	TABLET, FILM COATED	800 mg	ORAL	ANDA	20 sections
Cimetidine	HUMAN PRESCRIPTION DRUG LABEL	1	0093-8305	TABLET, FILM COATED	800 mg	ORAL	ANDA	20 sections
Cimetidine	HUMAN PRESCRIPTION DRUG LABEL	1	0093-8305	TABLET, FILM COATED	800 mg	ORAL	ANDA	20 sections

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