Details of the Drug

General Information of Drug (ID: DM20LIM)

Drug Name

Bremelanotide

Synonyms

Bremelanotide (USAN/INN); PT-141; Rekynda

Indication

Disease Entry	ICD 11	Status	REF
Hypoactive sexual desire dysfunction	HA00	Approved	[1]
Erectile dysfunction	HA01.1	Phase 3	[2]

Drug Type

Small molecular drug

Structure

3D MOL is unavailable

2D MOL

#Ro5 Violations (Lipinski): 4

Molecular Weight (mw)

1025.2

Topological Polar Surface Area (xlogp)

0.7

Rotatable Bond Count (rotbonds)

17

Hydrogen Bond Donor Count (hbonddonor)

13

Hydrogen Bond Acceptor Count (hbondacc)

12

ADMET Property

Absorption AUC: The area under the plot of plasma concentration (AUC) of drug is 276 mcgh/L [3]
Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 72.8 mcg/L [3]
Absorption Tmax: The time to maximum plasma concentration (Tmax) is 1.0 h [3]
Clearance: The clearance of drug is 6.5 +/- 1.0 L/h [3]
Elimination: 64.8% of a radiolabelled dose is excreted in the urine and 22.8% of the dose is recovered in the feces [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 2.7 hours [3]
Metabolism: The drug is metabolized via the multiple hydrolysis reactions [3]
Vd: The volume of distribution (Vd) of drug is 25.0 +/- 5.8 L [3]

Chemical Identifiers

Formula: C50H68N14O10
IUPAC Name: (3S,6S,9R,12S,15S,23S)-15-[[(2S)-2-acetamidohexanoyl]amino]-9-benzyl-6-[3-(diaminomethylideneamino)propyl]-12-(1H-imidazol-5-ylmethyl)-3-(1H-indol-3-ylmethyl)-2,5,8,11,14,17-hexaoxo-1,4,7,10,13,18-hexazacyclotricosane-23-carboxylic acid
Canonical SMILES: CCCC[C@@H](C(=O)N[C@H]1CC(=O)NCCCC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC1=O)CC2=CN=CN2)CC3=CC=CC=C3)CCCN=C(N)N)CC4=CNC5=CC=CC=C54)C(=O)O)NC(=O)C
InChI: InChI=1S/C50H68N14O10/c1-3-4-16-35(58-29(2)65)43(67)64-41-25-42(66)54-20-11-10-18-37(49(73)74)60-46(70)39(23-31-26-56-34-17-9-8-15-33(31)34)62-44(68)36(19-12-21-55-50(51)52)59-45(69)38(22-30-13-6-5-7-14-30)61-47(71)40(63-48(41)72)24-32-27-53-28-57-32/h5-9,13-15,17,26-28,35-41,56H,3-4,10-12,16,18-25H2,1-2H3,(H,53,57)(H,54,66)(H,58,65)(H,59,69)(H,60,70)(H,61,71)(H,62,68)(H,63,72)(H,64,67)(H,73,74)(H4,51,52,55)/t35-,36-,37-,38+,39-,40-,41-/m0/s1
InChIKey: FFHBJDQSGDNCIV-MFVUMRCOSA-N

Cross-matching ID

PubChem CID: 9941379
CAS Number: 189691-06-3
DrugBank ID: DB11653
TTD ID: D0X9PF
ACDINA ID: D00888

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Melanocortin receptor 1 (MC1R)	TT0MV2T	MSHR_HUMAN	Agonist	[1]
Melanocortin receptor 4 (MC4R)	TTD0CIQ	MC4R_HUMAN	Agonist	[1]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Hypoactive sexual desire dysfunction

ICD Disease Classification

HA00

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Melanocortin receptor 4 (MC4R)	DTT	MC4R	5.64E-01	-0.04	-0.18

Molecular Expression Atlas (MEA)

MEA Detail

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

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Hydrochloric acid	E00015	313	Acidulant
Glycerin	E00026	753	Antimicrobial preservative; Emollient; Flavoring agent; Humectant; Lubricant; Plasticizing agent; Solvent; Suppository base; Tonicity agent; Viscosity-controlling agent
Sodium hydroxide	E00234	14798	Alkalizing agent
Water	E00035	962	Solvent
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Bremelanotide 1.75 mg/0.3 ml Injection	1.75 mg/0.3 ml	Injection	Subcutaneous

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. 2019
2	Designing drugs for the treatment of female sexual dysfunction. Drug Discov Today. 2007 Sep;12(17-18):757-66.
3	FDA Approved Drug Products: Bremelanotide Injection
4	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2019
5	Interpreting expression profiles of cancers by genome-wide survey of breadth of expression in normal tissues. Genomics 2005 Aug;86(2):127-41.
6	Design of potent linear alpha-melanotropin 4-10 analogues modified in positions 5 and 10. J Med Chem. 1989 Jan;32(1):174-9.
7	Development of cyclic gamma-MSH analogues with selective hMC3R agonist and hMC3R/hMC5R antagonist activities. J Med Chem. 2006 Mar 23;49(6):1946-52.
8	Discovery of a beta-MSH-derived MC-4R selective agonist. J Med Chem. 2005 May 5;48(9):3095-8.
9	Structure-activity relationships of cyclic lactam analogues of alpha-melanocyte-stimulating hormone (alpha-MSH) targeting the human melanocortin-3 ... J Med Chem. 2008 Jan 24;51(2):187-95.
10	Emerging drugs for obesity: linking novel biological mechanisms to pharmaceutical pipelines. Expert Opin Emerg Drugs. 2005 Aug;10(3):643-60.
11	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2020
12	Novel anti-obesity drugs. Expert Opin Investig Drugs. 2000 Jun;9(6):1317-26.
13	Peptidomimetic C5a receptor antagonists with hydrophobic substitutions at the C-terminus: increased receptor specificity and in vivo activity. Bioorg Med Chem Lett. 2006 Oct 1;16(19):5088-92.
14	Melanocortin Receptor Agonists Facilitate Oxytocin-Dependent Partner Preference Formation in the Prairie Vole. Neuropsychopharmacology. 2015 Jul;40(8):1856-65.
15	The protective effects of the melanocortin receptor (MCR) agonist, melanotan-II (MTII), against binge-like ethanol drinking are facilitated by deletion of the MC3 receptor in mice. Neuropeptides. 2014 Feb;48(1):47-51.