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

Stem definition	Drug id	CAS RN
prostaglandins	1817	59122-46-2

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: misoprostol cytotec isprelor misoprost misoprostil	A synthetic analog of natural prostaglandin E1. It produces a dose-related inhibition of gastric acid and pepsin secretion, and enhances mucosal resistance to injury. It is an effective anti-ulcer agent and also has oxytocic properties. Molecular weight: 382.54 Formula: C22H38O5 CLOGP: 3.07 LIPINSKI: 0 HAC: 5 HDO: 2 TPSA: 83.83 ALOGS: -4.37 ROTB: 14 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

misoprostol
cytotec
isprelor
misoprost
misoprostil

A synthetic analog of natural prostaglandin E1. It produces a dose-related inhibition of gastric acid and pepsin secretion, and enhances mucosal resistance to injury. It is an effective anti-ulcer agent and also has oxytocic properties.

Molecular weight: 382.54
Formula: C22H38O5
CLOGP: 3.07
LIPINSKI: 0
HAC: 5
HDO: 2
TPSA: 83.83
ALOGS: -4.37
ROTB: 14

Status: OFP

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

Drug dosage:

Dose	Unit	Route
0.80	mg	O
0.20	mg	O
0.20	mg	V

ADMET properties:

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Property	Value	Reference
BA (Bioavailability)	80 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	0.50 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	0.03 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

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Approvals:

Date	Agency	Company	Orphan
Dec. 27, 1988	FDA	GD SEARLE LLC

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
Abortion incomplete	8920.59	14.64	1434	20565	1697	63465326
Haemorrhage	4565.16	14.64	1407	20592	59615	63407408
Pregnancy	1546.78	14.64	552	21447	36284	63430739
Endometritis	930.91	14.64	178	21821	840	63466183
Heavy menstrual bleeding	657.52	14.64	243	21756	17530	63449493
Anaemia	521.07	14.64	571	21428	292859	63174164
Muscle spasms	363.32	14.64	352	21647	155798	63311225
Induced abortion failed	312.59	14.64	57	21942	195	63466828
Exposure during pregnancy	275.49	14.64	303	21696	155244	63311779
Uterine rupture	204.73	14.64	52	21947	1034	63465989

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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
Foetal exposure during pregnancy	272.51	16.78	127	5179	37974	34913651
Maternal exposure during pregnancy	81.64	16.78	30	5276	4888	34946737
Anencephaly	70.54	16.78	13	5293	126	34951499
Nail bed bleeding	57.40	16.78	13	5293	370	34951255
Premature baby	56.78	16.78	36	5270	19597	34932028
Congenital hydrocephalus	55.13	16.78	10	5296	88	34951537
Pulmonary hypoplasia	48.92	16.78	12	5294	485	34951140
Poor weight gain neonatal	46.54	16.78	7	5299	15	34951610
Congenital megaureter	44.38	16.78	9	5297	149	34951476
Neonatal respiratory arrest	44.37	16.78	7	5299	23	34951602

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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
Abortion incomplete	9165.89	14.55	1423	21028	1641	79720296
Haemorrhage	4235.57	14.55	1392	21059	89726	79632211
Pregnancy	1787.64	14.55	542	21909	26309	79695628
Endometritis	968.93	14.55	172	22279	636	79721301
Heavy menstrual bleeding	734.74	14.55	236	22215	13775	79708162
Anaemia	429.46	14.55	574	21877	444441	79277496
Muscle spasms	382.07	14.55	347	22104	174383	79547554
Exposure during pregnancy	314.00	14.55	246	22205	100886	79621051
Induced abortion failed	247.89	14.55	44	22407	162	79721775
Uterine rupture	198.31	14.55	45	22406	676	79721261

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	A02BB01	ALIMENTARY TRACT AND METABOLISM DRUGS FOR ACID RELATED DISORDERS DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) Prostaglandins
ATC	G02AD06	GENITO URINARY SYSTEM AND SEX HORMONES OTHER GYNECOLOGICALS UTEROTONICS Prostaglandins
ATC	M01AE56	MUSCULO-SKELETAL SYSTEM ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS Propionic acid derivatives
CHEBI has role	CHEBI:36063	oxytocic agents
CHEBI has role	CHEBI:49201	anti-ulcer drugs
CHEBI has role	CHEBI:50691	abortifacient drug
FDA CS	M0017811	Prostaglandins E, Synthetic
FDA EPC	N0000175785	Prostaglandin E1 Analog
MeSH PA	D000019	Abortifacient Agents
MeSH PA	D000020	Abortifacient Agents, Nonsteroidal

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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
Postpartum hemorrhage	indication	47821001
Rheumatoid Arthritis in Patient at High Ulcer Risk	indication
Prevention of NSAID-Induced Gastric Ulcer	indication
Prevention of CMV Disease After Organ Transplant	indication
Osteoarthritis in Patients at High Ulcer Risk	indication
Ankylosing spondylitis	off-label use	9631008	DOID:7147
Peptic ulcer	off-label use	13200003	DOID:750
Duodenal ulcer disease	off-label use	51868009	DOID:1724
Cervical ripening procedure	off-label use	236959001
Pregnancy with abortive outcome	off-label use	363681007

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

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Acid dissociation constants calculated using MoKa v3.0.0

None

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
Prostaglandin E2 receptor EP3 subtype	GPCR	P43115	PE2R3_HUMAN	AGONIST	Ki	8.10	IUPHAR	CHEMBL
Prostaglandin E2 receptor EP2 subtype	GPCR	P43116	PE2R2_HUMAN	AGONIST	Ki	7.50	IUPHAR
Prostaglandin E2 receptor EP4 subtype	GPCR	P35408	PE2R4_HUMAN	AGONIST	Ki	7.60	IUPHAR
Prostaglandin F2-alpha receptor	GPCR	P43088	PF2R_HUMAN		Ki	5.03	PDSP

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External reference:

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ID	Source
001133	NDDF
0E43V0BB57	UNII
12Z0SU967A	UNII
151578	RXNORM
387242007	SNOMEDCT_US
4019313	VUID
4019313	VANDF
43684009	SNOMEDCT_US
44310	MMSL
445	MMSL

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
ARTHROTEC	HUMAN PRESCRIPTION DRUG LABEL	2	0025-1411	TABLET, FILM COATED	200 ug	ORAL	NDA	33 sections
ARTHROTEC	HUMAN PRESCRIPTION DRUG LABEL	2	0025-1411	TABLET, FILM COATED	200 ug	ORAL	NDA	33 sections
ARTHROTEC	HUMAN PRESCRIPTION DRUG LABEL	2	0025-1411	TABLET, FILM COATED	200 ug	ORAL	NDA	33 sections
ARTHROTEC	HUMAN PRESCRIPTION DRUG LABEL	2	0025-1421	TABLET, FILM COATED	200 ug	ORAL	NDA	33 sections
ARTHROTEC	HUMAN PRESCRIPTION DRUG LABEL	2	0025-1421	TABLET, FILM COATED	200 ug	ORAL	NDA	33 sections
ARTHROTEC	HUMAN PRESCRIPTION DRUG LABEL	2	0025-1421	TABLET, FILM COATED	200 ug	ORAL	NDA	33 sections
ARTHROTEC	HUMAN PRESCRIPTION DRUG LABEL	2	16590-024	TABLET, FILM COATED	200 ug	ORAL	NDA	31 sections
ARTHROTEC	HUMAN PRESCRIPTION DRUG LABEL	2	21695-425	TABLET, FILM COATED	200 ug	ORAL	NDA	30 sections
Cytotec	HUMAN PRESCRIPTION DRUG LABEL	1	0025-1451	TABLET	100 ug	ORAL	NDA	28 sections
Cytotec	HUMAN PRESCRIPTION DRUG LABEL	1	0025-1461	TABLET	200 ug	ORAL	NDA	28 sections

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