Details of the Drug

General Information of Drug (ID: DM15HAT)

Drug Name

Leuprorelin acetate

Synonyms

Leuprolide acetate; Leuplin (TN); Leuprorelin acetate (JAN); 5-oxoPro-His-Trp-Ser-Tyr-D-Leu-Leu-Arg-ProNHC2H5 dihydrate

Indication

Disease Entry	ICD 11	Status	REF
Prostate cancer	2C82.0	Approved	[1]

Drug Type

Small molecular drug

Structure

3D MOL is unavailable

2D MOL

#Ro5 Violations (Lipinski):
4

Molecular Weight

1269.4

Topological Polar Surface Area

Not Available

Rotatable Bond Count

Hydrogen Bond Donor Count

Hydrogen Bond Acceptor Count

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [2]
Clearance: The drug present in the plasma can be removed from the body at the rate of 2 mL/min/kg [3]
Elimination: 2% of drug is excreted from urine in the unchanged form [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 2.9 hours [3]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.01174 micromolar/kg/day [4]
Unbound Fraction: The unbound fraction of drug in plasma is 0.54% [3]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.38 L/kg [3]
Water Solubility: The ability of drug to dissolve in water is measured as 250 mg/mL [2]

Chemical Identifiers

Formula: C61H88N16O14
IUPAC Name: 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
Canonical SMILES: 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](CC2=CC=C(C=C2)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC3=CNC4=CC=CC=C43)NC(=O)[C@H](CC5=CN=CN5)NC(=O)[C@@H]6CCC(=O)N6.CC(=O)O
InChI: InChI=1S/C59H84N16O12.C2H4O2/c1-6-63-57(86)48-14-10-22-75(48)58(87)41(13-9-21-64-59(60)61)68-51(80)42(23-32(2)3)69-52(81)43(24-33(4)5)70-53(82)44(25-34-15-17-37(77)18-16-34)71-56(85)47(30-76)74-54(83)45(26-35-28-65-39-12-8-7-11-38(35)39)72-55(84)46(27-36-29-62-31-66-36)73-50(79)40-19-20-49(78)67-40;1-2(3)4/h7-8,11-12,15-18,28-29,31-33,40-48,65,76-77H,6,9-10,13-14,19-27,30H2,1-5H3,(H,62,66)(H,63,86)(H,67,78)(H,68,80)(H,69,81)(H,70,82)(H,71,85)(H,72,84)(H,73,79)(H,74,83)(H4,60,61,64);1H3,(H,3,4)/t40-,41-,42-,43+,44-,45-,46-,47-,48-;/m0./s1
InChIKey: RGLRXNKKBLIBQS-XNHQSDQCSA-N

Cross-matching ID

PubChem CID: 657180
ChEBI ID: CHEBI:63597
CAS Number: 74381-53-6
TTD ID: D04ASH
ACDINA ID: D01205

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Gonadotropin-releasing hormone receptor (GNRHR)	TT8R70G	GNRHR_HUMAN	Agonist	[5]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Acetic acid	E00002	176	Acidulant; Buffering agent
Benzyl alcohol	E00010	244	Antimicrobial preservative; Solvent
Lactic acid	E00020	612	Acidulant
Mannitol	E00103	6251	Diluent; Flavoring agent; Lyophilization aid; Plasticizing agent; Tonicity agent
Carboxymethylcellulose sodium	E00621	Not Available	Adsorbent; Binding agent; Disintegrant; Emulsifying agent; Suspending agent; Viscosity-controlling agent
Gelatin	E00630	Not Available	Other agent
Polysorbate 80	E00665	Not Available	Dispersing agent; Emollient; Emulsifying agent; Plasticizing agent; Solubilizing agent; Surfactant; Suspending agent
Sodium chloride	E00077	5234	Diluent; Tonicity agent
Sodium hydroxide	E00234	14798	Alkalizing agent
Water	E00035	962	Solvent
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⏷ Show the Full List of 10 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Leuprolide Acetate 7.5mg powder	7.5mg	Powder	Intramuscular
Leuprolide Acetate 1mg/0.2ml injectable	1mg/0.2ml	Injectable	Injection

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2	BDDCS applied to over 900 drugs
3	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5	Clinical pipeline report, company report or official report of Takeda (2009).
6	Use of cognitive behavior therapy for functional hypothalamic amenorrhea. Ann N Y Acad Sci. 2006 Dec;1092:114-29.
7	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2020
8	Age attenuates testosterone secretion driven by amplitude-varying pulses of recombinant human luteinizing hormone during acute gonadotrope inhibiti... J Clin Endocrinol Metab. 2007 Sep;92(9):3626-32.
9	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
10	Regulation of GnRH I receptor gene expression by the GnRH agonist triptorelin, estradiol, and progesterone in the gonadotroph-derived cell line alphaT3-1. Endocrine. 2006 Aug;30(1):139-44.
11	Reversible downregulation of endocrine and germinative testicular function (hormonal castration) in the dog with the GnRH-agonist azagly-nafarelin ... Theriogenology. 2009 Apr 15;71(7):1037-45.
12	Gonadotropin releasing hormone analogs induce apoptosis by extrinsic pathway involving p53 phosphorylation in primary cell cultures of human prostatic adenocarcinomas. Prostate. 2009 Jul 1;69(10):1025-33.
13	2018 FDA drug approvals.Nat Rev Drug Discov. 2019 Feb;18(2):85-89.
14	Iterative approach to the discovery of novel degarelix analogues: substitutions at positions 3, 7, and 8. Part II. J Med Chem. 2005 Jul 28;48(15):4851-60.
15	Stability of cytotoxic luteinizing hormone-releasing hormone conjugate (AN-152) containing doxorubicin 14-O-hemiglutarate in mouse and human serum in vitro: implications for the design of preclinicalstudies. Proc Natl Acad Sci U S A. 2000 Jan 18;97(2):829-34.