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
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 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
Foetal exposure during pregnancy 346.90 111.39 81 296 36790 29915311
Premature baby 140.72 111.39 34 343 16657 29935444

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 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)

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
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:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
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