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

Stem definitionDrug idCAS RN
pituitary hormone-release stimulating peptides 1868 76932-56-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • nafarelin
  • nafareline
  • nafarelin acetate
A potent synthetic agonist of GONADOTROPIN-RELEASING HORMONE with 3-(2-naphthyl)-D-alanine substitution at residue 6. Nafarelin has been used in the treatments of central PRECOCIOUS PUBERTY and ENDOMETRIOSIS.
  • Molecular weight: 1322.50
  • Formula: C66H83N17O13
  • CLOGP: -1.22
  • LIPINSKI: 3
  • HAC: 30
  • HDO: 17
  • TPSA: 472.13
  • ALOGS: -4.90
  • ROTB: 33

Drug dosage:

DoseUnitRoute
0.40 mg N

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 1 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 3 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.02 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 0.14 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 0.72 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.19 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 3.50 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Feb. 13, 1990 FDA GD SEARLE LLC

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
Ovarian hyperstimulation syndrome 286.01 73.82 41 186 3151 46682684

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 H01CA02 SYSTEMIC HORMONAL PREPARATIONS, EXCL. SEX HORMONES AND INSULINS
PITUITARY AND HYPOTHALAMIC HORMONES AND ANALOGUES
HYPOTHALAMIC HORMONES
Gonadotropin-releasing hormones
FDA MoA N0000175654 Gonadotropin Releasing Hormone Receptor Agonists
FDA EPC N0000175655 Gonadotropin Releasing Hormone Receptor Agonist
MeSH PA D005300 Fertility Agents, Female
MeSH PA D012102 Reproductive Control Agents
CHEBI has role CHEBI:50751 anti-estrogenic agent
CHEBI has role CHEBI:63533 gonadotrophin releasing hormone agonists

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Endometriosis indication 129103003
Precocious puberty indication 400179000
Alcoholism contraindication 7200002
Hypercholesterolemia contraindication 13644009
Hypertensive disorder contraindication 38341003 DOID:10763
Osteoporosis contraindication 64859006 DOID:11476
Intermenstrual bleeding - irregular contraindication 64996003
Diabetes mellitus contraindication 73211009 DOID:9351
Hyperglycemia contraindication 80394007 DOID:4195
Pregnancy, function contraindication 289908002
Osteopenia contraindication 312894000
Cardiovascular event risk contraindication 395112001
Breastfeeding (mother) contraindication 413712001
Obesity contraindication 414916001 DOID:9970
Smokes tobacco daily contraindication 449868002

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.65 acidic
pKa2 11.9 acidic
pKa3 12.8 acidic
pKa4 12.93 acidic
pKa5 13.31 acidic
pKa6 13.4 acidic
pKa7 13.73 acidic
pKa8 10.75 Basic
pKa9 6.69 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
Gonadotropin-releasing hormone receptor GPCR AGONIST Kd 9.70 WOMBAT-PK CHEMBL

External reference:

IDSource
4019848 VUID
N0000147934 NUI
D00990 KEGG_DRUG
86220-42-0 SECONDARY_CAS_RN
4019489 VANDF
4019848 VANDF
C0064906 UMLSCUI
CHEBI:7445 CHEBI
CHEMBL1201309 ChEMBL_ID
CHEMBL1200671 ChEMBL_ID
D017274 MESH_DESCRIPTOR_UI
DB00666 DRUGBANK_ID
3902 IUPHAR_LIGAND_ID
5402 INN_ID
1X0094V6JV UNII
25077405 PUBCHEM_CID
203147 RXNORM
5144 MMSL
d00574 MMSL
003536 NDDF
004783 NDDF
008316 NDDF
008317 NDDF
109046009 SNOMEDCT_US
109047000 SNOMEDCT_US
126196000 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Synarel HUMAN PRESCRIPTION DRUG LABEL 1 0025-0166 SPRAY, METERED 2 mg NULLSAL NDA 25 sections