Leuprolide Acetate
Basic information
- CAS
74381-53-6- Standard SMILES
CC(=O)O.CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](Cc1cnc[nH]1)NC(=O)[C@@H]1CCC(=O)N1- InChIKey
RGLRXNKKBLIBQS-XNHQSDQCSA-N- Molecular formula
- C61H88N16O14
- Average molar mass
- 1,269.4 g/mol
- Monoisotopic mass
- 1,268.66659154
Overview
Leuprolide Acetate can cause developmental toxicity, female reproductive toxicity and male reproductive toxicity according to state or federal government labeling requirements.
Names & identifiers
- Preferred name
- Leuprolide Acetate
- IUPAC
- acetic acid;(2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-[(2S)-2-(ethylcarbamoyl)pyrrolidin-1-yl]-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide
- English name
- Leuprorelin acetate
- Molecular formula
- C61H88N16O14
- Molecular weight
- 1269.45
Names & synonyms
Leuprolide acetateLeuprorelin acetate74381-53-6LupronLucrinCarcinilEnantoneLeuplinTrenantoneEligardProstapViadur
Show more names
LEUPROLIDELeuprolide acetate (Leuprorelin acetate)6-D-Leucine-9-(N-ethyl-L-prolinamide)-10-deglycinamideluteinizing Hormone-Releasing Factor Acetate(Pig)TPA-144DC-2-269
Lupron DepotAbbott-43818FensolviLupanetaProcrinTAP-144Lutrate depotUno-Enantone
Database identifiers
- CAS
74381-53-6- PubChem CID
- 657180
- DTXSID
DTXSID7049009- ChEMBL
Properties
Computed structural properties
- Topological polar surface area
- 469 Ų
- Hydrogen bond donors
- 16
- Hydrogen bond acceptors
- 16
- Rotatable bonds
- 32
- Heavy atoms
- 91
- Formal charge
- 0
- Complexity
- 2,420
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physicochemical properties
- Melting point
- 150 · 150-155°C
- storage temp.
- -20 °C · -20°C
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- color
- White to Off-White
- Merck
- 14 · 14,5457
- InChIKey
- RGLRXNKKBLIBQS-XNHQSDQCSA-N
- NCI Dictionary of Cancer Terms
- leuprolide acetate; Lupron
- FDA UNII
- 37 JNS02E7V · 37JNS02E7V
- NCI Drug Dictionary
- leuprolide acetate
- Proposition 65 List
- Leuprolide Acetate
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 32 · NA.32
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H317 (30.6%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P203, P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P317, P318, P321, P333+P317, P342+P316, P362+P364, P403, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 62 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationHazard Traits - Developmental Toxicity; Reproductive Toxicity
Hazard Classes and CategoriesSkin Sens. 1 (30.6%)
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Leuprolide acetate
vLess-DILI-concern
3
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 2
- rtecs
- OH6390000
- hs_code
- 29371900
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-24/25
- Storage Class
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
LEUPROLIDE ACETATE
Gonadotropin Releasing Hormone Receptor Agonist [EPC]; Gonadotropin Releasing Hormone Receptor Agonists [MoA]
MeSH Pharmacological Classification
Compounds which increase the capacity to conceive in females.
Antineoplastic agents that are used to treat hormone-sensitive tumors. Hormone-sensitive tumors may be hormone-dependent, hormone-responsive, or both. A hormone-dependent tumor regresses on removal of the hormonal stimulus, by surgery or pharmacological block. Hormone-responsive tumors may regress when pharmacologic amounts of hormones are administered regardless of whether previous signs of hormone sensitivity were observed. The major hormone-responsive cancers include carcinomas of the breast, prostate, and endometrium; lymphomas; and certain leukemias. (From AMA Drug Evaluations Annual 1994, p2079)
Uses & manufacturing
UsesUse (kg) in USA (2002): 1
Applications
DescriptionLeuprolide acetate is a potent analog of LH-RH useful in achieving a medical castration in the treatment of advanced prostate cancer. It has also been investigated for the treatment of advanced breast cancer.
UsesLeuprolide acetate USP (Leupron) is used to treat Prostatic carcinoma.
UsesSynthetic nonapeptide agonist analog of LH-RH. Antineoplastic (hormonal).
UsesIn mice, leuprolide acetate salt has been used to check the need of estrogen receptor α in spermatogenic cells, for development or function in fertilization.
Upstream & downstream products
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…