Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00394)
Name
Melphalan
Synonyms    Click to Show/Hide the Synonyms of This API
melphalan; 148-82-3; Alkeran; Melfalan; Phenylalanine mustard; L-Sarcolysine; L-Sarcolysin; p-L-Sarcolysin; Melphalanum; Melfalano; 4-[Bis(2-chloroethyl)amino]-L-phenylalanine; Phenylalanine nitrogen mustard; L-Phenylalanine mustard; Levofalan; p-Di-(2-chloroethyl)amino-L-phenylalanine; Levopholan; Levofolan; p-Bis(beta-chloroethyl)aminophenylalanine; 3-(p-(Bis(2-chloroethyl)amino)phenyl)-L-alanine; L-Sarkolysin; p-N-Bis(2-chloroethyl)amino-L-phenylalanine; 4-(Bis(2-chloroethyl)amino)-L-phenylalanine; CB 3025; 3-p-(Di(2-chloroethyl)amino)-phenyl-L-alanine; NCI-C04853; L-3-(p-(Bis(2-chloroethyl)amino)phenyl)alanine; Alanine Nitrogen Mustard; NSC-8806; (2S)-2-amino-3-[4-[bis(2-chloroethyl)amino]phenyl]propanoic acid; UNII-Q41OR9510P; CB-3025; CHEBI:28876; Melphalan (free base); p-N,N-bis(2-chloroethyl)amino-L-phenylalanine; CHEMBL852; SK 15673; Sarcolysinum; ALKERAN (TN); Rcra waste number U150; (S)-2-amino-3-(4-(bis(2-chloroethyl)amino)phenyl)propanoic acid; Q41OR9510P; 13045-94-8 (free base); Melphalan, 94%; Alanine, 3-(p-(bis(2-chloroethyl)amino)phenyl)-, L-; Alanine, 3-[p-[bis(2-chloroethyl)amino]phenyl]-, L-; SK-15673; NCGC00090757-02; DSSTox_CID_804; DSSTox_RID_75797; DSSTox_GSID_20804; Melfalano [INN-Spanish]; Melphalanum [INN-Latin]; Phenylalanine, 4-[bis(2-chloroethyl)amino]-; Evomela; (2s)-2-amino-3-(4-[bis(2-chloroethyl)amino]phenyl)propanoic acid; (S)-2-Amino-3-{4-[bis-(2-chloro-ethyl)-amino]-phenyl}-propionic acid; Melphalan-d8 Dihydrochloride; NSC8806; CAS-148-82-3; SMR000058720; CCRIS 374; HSDB 3234; EINECS 205-726-3; RCRA waste no. U150; NSC 241286; BRN 2816456; L-3-(para-(Bis(2-chloroethyl)amino)phenyl)alanine; Phelinun; (2S)-2-amino-3-{4-[bis(2-chloroethyl)amino]phenyl}propanoic acid; MFCD00057717; NSC241286; Melphalan, powder; NSC-241286; Prestwick_1006; Melphalan [USAN:USP:INN:BAN:JAN]; Spectrum_000397; 3025 C.B.; Spectrum2_000074; Spectrum3_000684; Spectrum4_000882; Spectrum5_001601; DL-Melphalan hydrochloride; 3-(p-(Bis(2-chloroethyl)amino)phenyl)alanine; Epitope ID:141802; 4-[Bis-(2-chloroethyl)amino]-L-phenylalanine; SCHEMBL5872; BSPBio_002407; KBioGR_001284; KBioSS_000877; 4-14-00-01689 (Beilstein Handbook Reference); MLS001333666; MLS002153368; BIDD:GT0044; DivK1c_000653; SPECTRUM1500382; SPBio_000287; Melphalan (JP17/USP/INN); GTPL7620; ZINC1673; DTXSID6020804; NIOSH/AY3360000; HMS502A15; KBio1_000653; KBio2_000877; KBio2_003445; KBio2_006013; KBio3_001627; L-phenylalanine mustard (L-PAM); NINDS_000653; HMS2090B09; HMS2091B16; HMS2235D21; Pharmakon1600-01500382; Tox21_111010; Tox21_202522; BDBM50025837; CCG-39704; DL-442; NSC757098; AKOS015895374; Tox21_111010_1; CS-3120; DB01042; NSC-757098; IDI1_000653; SMP2_000174; NCGC00090757-01; NCGC00090757-03; NCGC00090757-04; NCGC00090757-05; NCGC00090757-06; NCGC00260071-01; AS-13314; HY-17575; SBI-0052787.P003; AB0005221; AY33600000; 4-[bis(2-chloroethyl)-amino]-L-phenylalanine; 4-[bis(2-chloroethyl)-amino]-l-phenyl-alanine; 4-[bis(2-chloroethyl)amino]-(L)-phenylalanine; C07122; D00369; K-4728; AB00053282-07; AB00053282-08; AB00053282_09; 148M823; A808810; Alanine, 3-(p-(bis(2-chloroethyl)amino)phenyl)-; SR-05000001667; Q2298283; SR-05000001667-1; W-108096; BRD-K87827419-001-02-8; 2-amino-3-[4-bis(2-chloroethyl)amino]phenylpropanoic acid; UNII-A960M0G5TP component SGDBTWWWUNNDEQ-LBPRGKRZSA-N; (2S)-2-azanyl-3-[4-[bis(2-chloroethyl)amino]phenyl]propanoic acid; 2-Amino-3-{4-[bis-(2-chloro-ethyl)-amino]-phenyl}-propionic acid; 2-Amino-3-{4-[bis-(2-chloro-ethyl)-amino]-phenyl}-propionic acid(L-PAM); 2-Amino-3-{4-[bis-(2-chloro-ethyl)-amino]-phenyl}-propionic acid (Melphalan); 2-Amino-3-{4-[bis-(2-chloro-ethyl)-amino]-phenyl}-propionic acid(Melphalan)
Clinical Status
Approved
Disease Indication Multiple myeloma ICD-11: 2A83 [1]
PubChem CID
460612
Formula
C13H18Cl2N2O2
Canonical SMILES
C1=CC(=CC=C1C[C@@H](C(=O)O)N)N(CCCl)CCCl
InChI
1S/C13H18Cl2N2O2/c14-5-7-17(8-6-15)11-3-1-10(2-4-11)9-12(16)13(18)19/h1-4,12H,5-9,16H2,(H,18,19)/t12-/m0/s1
InChIKey
SGDBTWWWUNNDEQ-LBPRGKRZSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
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3D MOL 2D MOL
Physicochemical Properties Molecular Weight 305.2 Topological Polar Surface Area 66.6
XlogP -0.5 Complexity 265
Heavy Atom Count 19 Rotatable Bond Count 8
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Full List of Drug Formulations (DFMs) Containing This API
          Melphalan 2 mg tablet Click to Show/Hide the Full List of Formulation(s):          2 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Magnesium stearate; Titanium dioxide; Crospovidone; Polyethylene glycol 400; Silicon dioxide; Cellulose, microcrystalline; Hypromelloses
                   Dosage Form Oral Tablet
                   Company ApoPharma USA
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [2]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [2]
Polyethylene glycol 400 DIG Info Albendazole monooxygenase (IC50 = 10.77 mg.mL-1) [3]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [2]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Magnesium stearate; Titanium dioxide; Silicon dioxide; Crospovidone (15 mpa.s at 5%); Hypromellose, unspecified; Microcrystalline cellulose; Polyethylene glycol, unspecified
                   Dosage Form Oral Tablet
                   Company Alvogen
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [2]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [2]
References
1 FDA label for approved melphalan from the official website of the U.S. Food and Drug Administration.
2 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
3 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.

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