oxytocin Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
oxytocin derivatives	2042	50-56-6

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: oxytocin orasthin oxystin partocon perlacton synthetic oxytocin	A nonapeptide hormone released from the neurohypophysis (PITUITARY GLAND, POSTERIOR). It differs from VASOPRESSIN by two amino acids at residues 3 and 8. Oxytocin acts on SMOOTH MUSCLE CELLS, such as causing UTERINE CONTRACTIONS and MILK EJECTION. Molecular weight: 1007.19 Formula: C43H66N12O12S2 CLOGP: -0.65 LIPINSKI: 3 HAC: 24 HDO: 12 TPSA: 399.53 ALOGS: -4.26 ROTB: 17 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

oxytocin
orasthin
oxystin
partocon
perlacton
synthetic oxytocin

A nonapeptide hormone released from the neurohypophysis (PITUITARY GLAND, POSTERIOR). It differs from VASOPRESSIN by two amino acids at residues 3 and 8. Oxytocin acts on SMOOTH MUSCLE CELLS, such as causing UTERINE CONTRACTIONS and MILK EJECTION.

Molecular weight: 1007.19
Formula: C43H66N12O12S2
CLOGP: -0.65
LIPINSKI: 3
HAC: 24
HDO: 12
TPSA: 399.53
ALOGS: -4.26
ROTB: 17

Status: OFP

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

Drug dosage:

Dose	Unit	Route
15	U	N
200	U	O
15	U	P

ADMET properties:

None

Approvals:

Date	Agency	Company	Orphan
April 17, 1980	FDA	NOVARTIS

FDA Adverse Event Reporting System (Female)

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
Exposure during pregnancy	716.30	34.41	289	3823	107923	46574027
Postpartum haemorrhage	475.68	34.41	89	4023	1708	46680242
Maternal exposure during pregnancy	404.96	34.41	191	3921	102358	46579592
Caesarean section	202.83	34.41	70	4042	16533	46665417
Uterine atony	199.10	34.41	30	4082	135	46681815
Maternal exposure during delivery	194.26	34.41	37	4075	779	46681171
Hypotension	181.39	34.41	155	3957	232434	46449516
Uterine rupture	120.44	34.41	26	4086	1038	46680912
Premature delivery	108.12	34.41	48	4064	22021	46659929
Foetal exposure during pregnancy	104.66	34.41	52	4060	30695	46651255
Pre-eclampsia	90.95	34.41	32	4080	7962	46673988
Normal newborn	87.77	34.41	29	4083	5972	46675978
Electrocardiogram ST segment depression	87.11	34.41	24	4088	2669	46679281
Anaphylactic reaction	75.78	34.41	51	4061	53061	46628889
Drug ineffective	74.56	34.41	175	3937	677663	46004287
Anaphylactoid syndrome of pregnancy	69.78	34.41	10	4102	29	46681921
Placenta accreta	61.37	34.41	11	4101	163	46681787
Amniotic cavity infection	59.74	34.41	15	4097	1163	46680787
Stillbirth	55.30	34.41	21	4091	6470	46675480
Low birth weight baby	55.18	34.41	20	4092	5414	46676536
Premature baby	53.91	34.41	28	4084	18084	46663866
Bradycardia foetal	52.91	34.41	11	4101	365	46681585
Premature rupture of membranes	51.42	34.41	18	4094	4405	46677545
Uterine haemorrhage	50.96	34.41	17	4095	3600	46678350
Retained placenta or membranes	49.95	34.41	10	4102	274	46681676
Pulmonary oedema	47.70	34.41	38	4074	51067	46630883
Vascular resistance systemic decreased	45.53	34.41	8	4104	105	46681845
Tachycardia	44.25	34.41	49	4063	99573	46582377
Cardiac output increased	43.65	34.41	8	4104	135	46681815
Mean arterial pressure decreased	42.75	34.41	8	4104	152	46681798
Endometritis	42.44	34.41	11	4101	968	46680982
Gestational diabetes	39.53	34.41	17	4095	7202	46674748
Small for dates baby	39.23	34.41	14	4098	3623	46678327
Disseminated intravascular coagulation	39.00	34.41	23	4089	18982	46662968
Gestational hypertension	37.97	34.41	12	4100	2143	46679807
Vaginal haemorrhage	37.46	34.41	25	4087	25579	46656371
Hypothermia	36.72	34.41	19	4093	12164	46669786
Uterine hypertonus	36.22	34.41	7	4105	159	46681791
Stroke volume increased	36.20	34.41	5	4107	10	46681940

FDA Adverse Event Reporting System (Male)

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	346.90	111.39	81	296	36790	29915311
Premature baby	140.72	111.39	34	343	16657	29935444

Pharmacologic Action:

Source	Code	Description
ATC	G02AC01	GENITO URINARY SYSTEM AND SEX HORMONES OTHER GYNECOLOGICALS UTEROTONICS Ergot alkaloids and oxytocin incl. analogues, in combination
ATC	H01BB02	SYSTEMIC HORMONAL PREPARATIONS, EXCL. SEX HORMONES AND INSULINS PITUITARY AND HYPOTHALAMIC HORMONES AND ANALOGUES POSTERIOR PITUITARY LOBE HORMONES Oxytocin and analogues
FDA CS	M0015703	Oxytocin
FDA PE	N0000009705	Increased Uterine Smooth Muscle Contraction or Tone
CHEBI has role	CHEBI:35620	vasodilator
CHEBI has role	CHEBI:36063	oxytocic
FDA EPC	N0000175828	Oxytocic
MeSH PA	D010120	Oxytocics
MeSH PA	D012102	Reproductive Control Agents

Drug Use (View source of the data)

Disease	Relation	SNOMED_ID	DOID
Postpartum hemorrhage	indication	47821001
Incomplete miscarriage	indication	156072005
Induction of labor	indication	236958009
Pregnancy with abortive outcome	indication	363681007
Placental Reserve Studies	off-label use
Multiple pregnancy	contraindication	16356006
Grand multipara	contraindication	18656007
Placenta previa	contraindication	36813001	DOID:11060
Hypertensive disorder	contraindication	38341003	DOID:10763
Fetal distress	contraindication	130955003
Deliveries by cesarean	contraindication	200144004
Finding of malposition of fetus	contraindication	289365005

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	9.65	acidic
pKa2	12.47	acidic
pKa3	12.94	acidic
pKa4	13.18	acidic
pKa5	13.47	acidic
pKa6	13.7	acidic
pKa7	13.89	acidic
pKa8	6.4	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Oxytocin receptor	GPCR	P30559	OXYR_HUMAN	AGONIST	Ki	9.10	CHEMBL	CHEMBL
Vasopressin V2 receptor	GPCR	P30518	V2R_HUMAN		EC50	6.10	WOMBAT-PK
Vasopressin V1b receptor	GPCR	P47901	V1BR_HUMAN		EC50	6.35	WOMBAT-PK
Vasopressin V1a receptor	GPCR	P37288	V1AR_HUMAN		EC50	6.91	WOMBAT-PK
Oxytocin-neurophysin 1	Secreted	P01178	NEU1_HUMAN				WOMBAT-PK
Vasopressin V2 receptor	GPCR		V2R_RAT		Ki	7.21	CHEMBL
Oxytocin receptor	GPCR		OXYR_RAT		Ki	9.05	CHEMBL
Vasopressin V1a receptor	GPCR		V1AR_RAT	AGONIST	Ki	6.10	IUPHAR

External reference:

ID	Source
4018039	VUID
N0000146381	NUI
D00089	KEGG_DRUG
4018039	VANDF
C0030095	UMLSCUI
CHEBI:7872	CHEBI
CHEMBL395429	ChEMBL_ID
D010121	MESH_DESCRIPTOR_UI
DB00107	DRUGBANK_ID
2174	IUPHAR_LIGAND_ID
1480	INN_ID
1JQS135EYN	UNII
439302	PUBCHEM_CID
7824	RXNORM
4537	MMSL
5223	MMSL
d00584	MMSL
001307	NDDF
112115002	SNOMEDCT_US
12369008	SNOMEDCT_US

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Oxytocin	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9742	INJECTION	10 [USPU]	INTRAMUSCULAR	ANDA	20 sections
Oxytocin	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9743	INJECTION	10 [USPU]	INTRAMUSCULAR	ANDA	20 sections
Oxytocin	HUMAN PRESCRIPTION DRUG LABEL	1	0641-6114	INJECTION	10 [USPU]	INTRAMUSCULAR	NDA	20 sections
Oxytocin	HUMAN PRESCRIPTION DRUG LABEL	1	0641-6115	INJECTION	10 [USPU]	INTRAMUSCULAR	NDA	20 sections
Pitocin	HUMAN PRESCRIPTION DRUG LABEL	1	42023-116	INJECTION	10 [iU]	INTRAVENOUS	NDA	22 sections
Pitocin	HUMAN PRESCRIPTION DRUG LABEL	1	42023-130	INJECTION	10 [iU]	INTRAVENOUS	NDA	22 sections
Oxytocin	HUMAN PRESCRIPTION DRUG LABEL	1	52533-048	INJECTION, SOLUTION	10 [USPU]	INTRAVENOUS	unapproved drug other	1 sections
Oxytocin	HUMAN PRESCRIPTION DRUG LABEL	1	52533-051	INJECTION, SOLUTION	2 [USPU]	INTRAVENOUS	unapproved drug other
Oxytocin	HUMAN PRESCRIPTION DRUG LABEL	1	52533-054	INJECTION, SOLUTION	30 [USPU]	INTRAVENOUS	unapproved drug other
Oxytocin	HUMAN PRESCRIPTION DRUG LABEL	1	52533-055	INJECTION, SOLUTION	30 [USPU]	INTRAVENOUS	unapproved drug other
Oxytocin	HUMAN PRESCRIPTION DRUG LABEL	1	52533-056	INJECTION, SOLUTION	15 [USPU]	INTRAVENOUS	unapproved drug other	1 sections
Oxytocin	HUMAN PRESCRIPTION DRUG LABEL	1	52533-056	INJECTION, SOLUTION	30 [USPU]	INTRAVENOUS	unapproved drug other	1 sections
Oxytocin	HUMAN PRESCRIPTION DRUG LABEL	1	52533-105	INJECTION, SOLUTION	2 [USPU]	INTRAVENOUS	unapproved drug other
Oxytocin	HUMAN PRESCRIPTION DRUG LABEL	1	52533-170	INJECTION, SOLUTION	30 [USPU]	INTRAVENOUS	unapproved drug other
Oxytocin	HUMAN PRESCRIPTION DRUG LABEL	1	52533-233	INJECTION, SOLUTION	20 [USPU]	INTRAVENOUS	unapproved drug other	1 sections
Oxytocin	HUMAN PRESCRIPTION DRUG LABEL	1	52533-234	INJECTION, SOLUTION	30 [USPU]	INTRAVENOUS	unapproved drug other	1 sections
Oxytocin	HUMAN PRESCRIPTION DRUG LABEL	1	55154-9584	INJECTION, SOLUTION	10 [USPU]	INTRAVENOUS	NDA	12 sections
Oxytocin	HUMAN PRESCRIPTION DRUG LABEL	1	63323-012	INJECTION, SOLUTION	10 [USPU]	INTRAVENOUS	NDA	12 sections
Oxytocin	HUMAN PRESCRIPTION DRUG LABEL	1	63323-012	INJECTION, SOLUTION	10 [USPU]	INTRAVENOUS	NDA	12 sections