melphalan 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
	1678	148-82-3

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: melphalan hydrochloride melphalan alkeran levofalan levofolan levopholan melfalan phenylalanine mustard sarcoclorin melphalan HCl	An alkylating nitrogen mustard that is used as an antineoplastic in the form of the levo isomer - MELPHALAN, the racemic mixture - MERPHALAN, and the dextro isomer - MEDPHALAN; toxic to bone marrow, but little vesicant action; potential carcinogen. Molecular weight: 305.20 Formula: C13H18Cl2N2O2 CLOGP: -0.21 LIPINSKI: 0 HAC: 4 HDO: 2 TPSA: 66.56 ALOGS: -2.93 ROTB: 8 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

melphalan hydrochloride
melphalan
alkeran
levofalan
levofolan
levopholan
melfalan
phenylalanine mustard
sarcoclorin
melphalan HCl

An alkylating nitrogen mustard that is used as an antineoplastic in the form of the levo isomer - MELPHALAN, the racemic mixture - MERPHALAN, and the dextro isomer - MEDPHALAN; toxic to bone marrow, but little vesicant action; potential carcinogen.

Molecular weight: 305.20
Formula: C13H18Cl2N2O2
CLOGP: -0.21
LIPINSKI: 0
HAC: 4
HDO: 2
TPSA: 66.56
ALOGS: -2.93
ROTB: 8

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

None

ADMET properties:

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Property	Value	Reference
BA (Bioavailability)	71 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
CL (Clearance)	7 mL/min/kg	Lombardo F, Berellini G, Obach RS
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Bocci G, Oprea TI, Benet LZ
EoM (Fraction excreted unchanged in urine)	12 %	Benet LZ, Broccatelli F, Oprea TI
t_half (Half-life)	1 hours	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	0.48 L/kg	Lombardo F, Berellini G, Obach RS
MRTD (Maximum Recommended Therapeutic Daily Dose)	0.33 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
fu (Fraction unbound in plasma)	0.14 %	Lombardo F, Berellini G, Obach RS
S (Water solubility)	0.01 mg/mL	Bocci G, Oprea TI, Benet LZ

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Approvals:

Date	Agency	Company	Orphan
Jan. 17, 1964	FDA	GLAXOSMITHKLINE

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Mucosal inflammation	657.39	19.47	337	25024	46591	63417070
Acute graft versus host disease	608.46	19.47	170	25191	4258	63459403
Graft versus host disease	471.80	19.47	154	25207	6609	63457052
Venoocclusive liver disease	457.70	19.47	139	25222	4696	63458965
Myelodysplastic syndrome	436.41	19.47	185	25176	16569	63447092
Adenovirus infection	435.87	19.47	125	25236	3446	63460215
Thrombotic microangiopathy	426.40	19.47	160	25201	10401	63453260
Febrile neutropenia	419.79	19.47	360	25001	118089	63345572
Acute graft versus host disease in skin	321.40	19.47	98	25263	3354	63460307
Neutropenia	304.90	19.47	362	24999	174643	63289018

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Venoocclusive liver disease	619.05	16.63	242	31036	7724	34917929
Acute graft versus host disease	614.98	16.63	228	31050	6275	34919378
Mucosal inflammation	606.42	16.63	396	30882	38226	34887427
Myelodysplastic syndrome	564.92	16.63	296	30982	18912	34906741
Acute myeloid leukaemia	435.45	16.63	245	31033	18025	34907628
Febrile neutropenia	371.68	16.63	530	30748	136319	34789334
Graft versus host disease	360.25	16.63	180	31098	10389	34915264
Acute graft versus host disease in skin	324.56	16.63	135	31143	5066	34920587
Chronic graft versus host disease	241.21	16.63	104	31174	4269	34921384
Thrombotic microangiopathy	217.09	16.63	129	31149	10501	34915152

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Acute graft versus host disease	1106.06	16.62	360	48763	9807	79685458
Venoocclusive liver disease	1038.68	16.62	356	48767	11415	79683850
Mucosal inflammation	1019.54	16.62	614	48509	74966	79620299
Myelodysplastic syndrome	914.26	16.62	422	48701	29879	79665386
Graft versus host disease	774.64	16.62	306	48817	14720	79680545
Acute graft versus host disease in skin	622.83	16.62	218	48905	7440	79687825
Acute myeloid leukaemia	611.67	16.62	323	48800	30562	79664703
Febrile neutropenia	599.62	16.62	724	48399	230275	79464990
Thrombotic microangiopathy	559.00	16.62	265	48858	19904	79675361
Adenovirus infection	539.05	16.62	201	48922	8246	79687019

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	L01AA03	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS ANTINEOPLASTIC AGENTS ALKYLATING AGENTS Nitrogen mustard analogues
CHEBI has role	CHEBI:35610	antineoplastic agents
CHEBI has role	CHEBI:35705	immunosuppressive agents
CHEBI has role	CHEBI:50903	carcinogen
CHEBI has role	CHEBI:88188	allergenic drug
FDA EPC	N0000175558	Alkylating Drug
FDA MoA	N0000000236	Alkylating Activity
MeSH PA	D000477	Alkylating Agents
MeSH PA	D000970	Antineoplastic Agents
MeSH PA	D018906	Antineoplastic Agents, Alkylating

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Multiple myeloma	indication	109989006	DOID:9538
Malignant tumor of ovary	indication	363443007	DOID:2394
Allogeneic bone marrow transplantation	off-label use	58390007
Diffuse non-Hodgkin's lymphoma, large cell	off-label use	109969005
Acute hemorrhage	contraindication	8573003
Vasculitis	contraindication	31996006	DOID:865
Fibrosis of lung	contraindication	51615001	DOID:3770
Portal vein obstruction	contraindication	57348003
Hemolytic anemia	contraindication	61261009	DOID:583
Acute infectious disease	contraindication	63171007

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	2.27	acidic
pKa2	9.25	Basic
pKa3	4.94	Basic

Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
EQ 50MG BASE/VIAL	EVOMELA	ACROTECH BIOPHARMA	N207155	March 10, 2016	RX	POWDER	INTRAVENOUS	10940128	June 14, 2030	FOR HIGH-DOSE CONDITIONING TREATMENT PRIOR TO HEMATOPOIETIC PROGENITOR (STEM) CELL TRANSPLANTATION IN PATIENTS WITH MULTIPLE MYELOMA

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Orange Book exclusivity data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
EQ 50MG BASE/VIAL	EVOMELA	ACROTECH BIOPHARMA	N207155	March 10, 2016	RX	POWDER	INTRAVENOUS	March 10, 2023	FOR HIGH-DOSE CONDITIONING TREATMENT PRIOR TO HEMATOPOIETIC PROGENITOR (STEM) CELL TRANSPLANTATION IN PATIENTS WITH MULTIPLE MYELOMA

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
L-type amino acid transporter 1	Transporter		LAT1_RAT		Ki	4.26		CHEMBL

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External reference:

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ID	Source
002633	NDDF
004144	NDDF
151325	RXNORM
167596	MMSL
1789	MMSL
31570	MMSL
3223-07-2	SECONDARY_CAS_RN
387297002	SNOMEDCT_US
4018763	VANDF
4020558	VUID

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
ALKERAN	HUMAN PRESCRIPTION DRUG LABEL	1	52609-0001	TABLET, FILM COATED	2 mg	ORAL	NDA	24 sections
EVOMELA	Human Prescription Drug Label	1	68152-109	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	NDA	26 sections
EVOMELA	Human Prescription Drug Label	1	72893-001	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	NDA	26 sections
EVOMELA	Human Prescription Drug Label	1	72893-001	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	NDA	26 sections
EVOMELA	Human Prescription Drug Label	1	72893-001	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	NDA	26 sections
EVOMELA	Human Prescription Drug Label	1	72893-001	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	NDA	26 sections
Melphalan	HUMAN PRESCRIPTION DRUG LABEL	1	47781-200	TABLET	2 mg	ORAL	ANDA	22 sections
Melphalan	HUMAN PRESCRIPTION DRUG LABEL	1	47781-200	TABLET	2 mg	ORAL	ANDA	22 sections
Melphalan Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	71681-002	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	26 sections

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