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Substance Name: Nafarelin acetate
RN: 76932-60-0
UNII: TH2HMT9YBQ
InChIKey: GUJYDLHACHDKAJ-CFWZQLQRSA-N

Note

  • 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 Formula

  • C66-H83-N17-O13.x-C2-H4-O2

Molecular Weight

  • 1382.5393
 

Classification Codes

  • Drug / Therapeutic Agent
  • Fertility Agents
  • Fertility Agents, Female
  • Hormone
  • Human Data
  • Reproductive Control Agents
  • Reproductive Effect

Names and Synonyms

Results Name

  • Nafarelin acetate

Name of Substance

  • Nafarelin acetate anhydrous

Synonyms

  • (6-D-(2-Naphthyl)alanine)LHRH acetate
  • (6-D-(2-Naphthyl)alanine)luteinizing hormone-releasing hormone acetate
  • Luteinizing hormone-releasing hormone, (6-D-(2-naphthyl)alanine)-, acetate
  • Nafarelin acetate
  • Synarel
  • Synarela
  • UNII-TH2HMT9YBQ

Systematic Names

  • Luteinizing hormone-releasing factor (pig), 6-(3-(2-naphthalenyl)-D-alanine)-, monoacetate (salt)
  • Luteinizing hormone-releasing factor (swine), 6-(3-(2-naphthalenyl)-D-alanine)-, monoacetate (salt)

Registry Numbers

CAS Registry Number

  • 76932-60-0

FDA UNII

  • TH2HMT9YBQ

Other Registry Numbers

  • 121897-31-2
  • 144949-01-9
  • 78115-72-7

Related Registry Number

  • 76932-56-4 (Parent)

System Generated Number

  • 0076932600

Molecular Formulas

Molecular Formula

  • C66-H83-N17-O13.x-C2-H4-O2

Molecular Formula Fragments

  • C2-H4-O2
  • C66-H83-N17-O13
  • COMPONENT

Structure Descriptors

InChI

1S/C66H83N17O13.C2H4O2/c1-36(2)25-48(58(89)76-47(13-7-23-71-66(68)69)65(96)83-24-8-14-54(83)64(95)73-33-55(67)86)77-60(91)50(28-38-15-18-39-9-3-4-10-40(39)26-38)78-59(90)49(27-37-16-19-43(85)20-17-37)79-63(94)53(34-84)82-61(92)51(29-41-31-72-45-12-6-5-11-44(41)45)80-62(93)52(30-42-32-70-35-74-42)81-57(88)46-21-22-56(87)75-46;1-2(3)4/h3-6,9-12,15-20,26,31-32,35-36,46-54,72,84-85H,7-8,13-14,21-25,27-30,33-34H2,1-2H3,(H2,67,86)(H,70,74)(H,73,95)(H,75,87)(H,76,89)(H,77,91)(H,78,90)(H,79,94)(H,80,93)(H,81,88)(H,82,92)(H4,68,69,71);1H3,(H,3,4)/t46-,47-,48-,49-,50+,51-,52-,53-,54-;/m0./s1

InChIKey

GUJYDLHACHDKAJ-CFWZQLQRSA-N

Smiles

CC(C)C[C@H](NC(=O)[C@@H](Cc1ccc2ccccc2c1)NC(=O)[C@H](Cc3ccc(O)cc3)NC(=O)[C@H](CO)NC(=O)[C@H](Cc4c[nH]c5ccccc45)NC(=O)[C@H](Cc6c[nH]cn6)NC(=O)[C@@H]7CCC(=O)N7)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N8CCC[C@H]8C(=O)NCC(=O)N.CC(=O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 subcutaneous 500ug/kg (0.5mg/kg)   Drugs in Japan Vol. -, Pg. 905, 1995.
monkey LD50 subcutaneous 500ug/kg (0.5mg/kg)   Drugs in Japan Vol. -, Pg. 905, 1995.
mouse LD50 intraperitoneal > 500ug/kg (0.5mg/kg)   Drugs in Japan Vol. -, Pg. 905, 1995.
mouse LD50 oral > 100mg/kg (100mg/kg)   Drugs in Japan Vol. -, Pg. 905, 1995.
mouse LD50 subcutaneous > 500ug/kg (0.5mg/kg)   Drugs in Japan Vol. -, Pg. 905, 1995.
rat LD50 intraperitoneal 500ug/kg (0.5mg/kg)   Drugs in Japan Vol. -, Pg. 905, 1995.
rat LD50 oral > 50mg/kg (50mg/kg)   Drugs in Japan Vol. -, Pg. 905, 1995.
rat LD50 subcutaneous 500ug/kg (0.5mg/kg)   Drugs in Japan Vol. -, Pg. 905, 1995.
women TCLo inhalation 368ug/kg (0.368mg/kg) PERIPHERAL NERVE AND SENSATION: PARESTHESIS Fertility and Sterility. Vol. 56, Pg. 357, 1991.