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

Stem definitionDrug idCAS RN
oxytocin derivatives 2042 50-56-6

Description:

MoleculeDescription

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:

DoseUnitRoute
15 U N
200 U O
15 U P

ADMET properties:

None

Approvals:

DateAgencyCompanyOrphan
April 17, 1980 FDA NOVARTIS

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Postpartum haemorrhage 459.48 100.39 59 387 311 2357328
Exposure during pregnancy 322.30 100.39 82 364 25137 2332502
Maternal exposure during pregnancy 252.29 100.39 61 385 14802 2342837
Hypotension 205.08 100.39 61 385 32375 2325264
Drug ineffective 174.13 100.39 72 374 101552 2256087
Uterine atony 171.54 100.39 21 425 65 2357574
Electrocardiogram ST segment depression 168.38 100.39 26 420 556 2357083
Caesarean section 129.03 100.39 28 418 4053 2353586
Maternal exposure during delivery 122.93 100.39 17 429 160 2357479
Pulmonary oedema 107.56 100.39 27 419 7336 2350303

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event

Pharmacologic Action:

SourceCodeDescription
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 PE N0000009705 Increased Uterine Smooth Muscle Contraction or Tone
FDA Chemical/Ingredient N0000006473 Oxytocin
MeSH PA D010120 Oxytocics
MeSH PA D012102 Reproductive Control Agents
CHEBI has role CHEBI:36063 oxytocic
CHEBI has role CHEBI:35620 vasodilator agent

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
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 levelDissociation constantType (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:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Oxytocin receptor GPCR AGONIST Ki 9.10 CHEMBL CHEMBL
Vasopressin V2 receptor GPCR EC50 6.10 WOMBAT-PK
Vasopressin V1b receptor GPCR EC50 6.35 WOMBAT-PK
Vasopressin V1a receptor GPCR EC50 6.91 WOMBAT-PK
Oxytocin-neurophysin 1 Secreted WOMBAT-PK
Vasopressin V2 receptor GPCR Ki 7.21 CHEMBL
Oxytocin receptor GPCR Ki 9.05 CHEMBL
Vasopressin V1a receptor GPCR AGONIST Ki 6.10 IUPHAR

External reference:

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

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Oxytocin HUMAN PRESCRIPTION DRUG LABEL 1 0143-9742 INJECTION 10 [USP'U] INTRAMUSCULAR ANDA 12 sections
Oxytocin HUMAN PRESCRIPTION DRUG LABEL 1 0143-9743 INJECTION 10 [USP'U] INTRAMUSCULAR ANDA 12 sections
Oxytocin HUMAN PRESCRIPTION DRUG LABEL 1 0641-6114 INJECTION 10 [USP'U] INTRAMUSCULAR NDA 12 sections
Oxytocin HUMAN PRESCRIPTION DRUG LABEL 1 0641-6115 INJECTION 10 [USP'U] INTRAMUSCULAR NDA 12 sections
Pitocin HUMAN PRESCRIPTION DRUG LABEL 1 42023-116 INJECTION 10 [iU] INTRAVENOUS NDA 13 sections
Pitocin HUMAN PRESCRIPTION DRUG LABEL 1 42023-130 INJECTION 10 [iU] INTRAVENOUS NDA 13 sections
Oxytocin HUMAN PRESCRIPTION DRUG LABEL 1 52533-048 INJECTION, SOLUTION 10 [USP'U] INTRAVENOUS unapproved drug other
Oxytocin HUMAN PRESCRIPTION DRUG LABEL 1 52533-051 INJECTION, SOLUTION 2 [USP'U] INTRAVENOUS unapproved drug other
Oxytocin HUMAN PRESCRIPTION DRUG LABEL 1 52533-054 INJECTION, SOLUTION 30 [USP'U] INTRAVENOUS unapproved drug other
Oxytocin HUMAN PRESCRIPTION DRUG LABEL 1 52533-055 INJECTION, SOLUTION 30 [USP'U] INTRAVENOUS unapproved drug other
Oxytocin HUMAN PRESCRIPTION DRUG LABEL 1 52533-056 INJECTION, SOLUTION 30 [USP'U] INTRAVENOUS unapproved drug other
Oxytocin HUMAN PRESCRIPTION DRUG LABEL 1 52533-105 INJECTION, SOLUTION 2 [USP'U] INTRAVENOUS unapproved drug other
Oxytocin HUMAN PRESCRIPTION DRUG LABEL 1 52533-170 INJECTION, SOLUTION 30 [USP'U] INTRAVENOUS unapproved drug other
Oxytocin HUMAN PRESCRIPTION DRUG LABEL 1 52533-233 INJECTION, SOLUTION 20 [USP'U] INTRAVENOUS unapproved drug other
Oxytocin HUMAN PRESCRIPTION DRUG LABEL 1 52533-234 INJECTION, SOLUTION 30 [USP'U] INTRAVENOUS unapproved drug other
Oxytocin HUMAN PRESCRIPTION DRUG LABEL 1 55154-9356 INJECTION, SOLUTION 10 [USP'U] INTRAVENOUS NDA 12 sections
Oxytocin HUMAN PRESCRIPTION DRUG LABEL 1 55154-9577 INJECTION, SOLUTION 10 [USP'U] INTRAVENOUS NDA 12 sections
Oxytocin HUMAN PRESCRIPTION DRUG LABEL 1 63323-012 INJECTION, SOLUTION 10 [USP'U] INTRAVENOUS NDA 12 sections