Rusfertide

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Also known as: Rusfertide [usan], Xm71myx0iq, Ptg-300fb, Ptg-300, 1628323-80-7, Isovaleryl-asp-thr-his-phe-pro-cyclo(cys-ile-lys(palm-gamma-glu)- phe-glu-pro-arg-ser-lys-gly-cys)-lys-nh2

Molecular Formula

C₁₁₄H₁₈₁N₂₇O₂₈S₂

Molecular Weight

2442.0 g/mol

InChI Key

JRVOBXXOZFTSRF-GVIPULMVSA-N

FDA UNII

XM71MYX0IQ

Rusfertide is an injectable peptide mimetic of hepcidin (hepcidin antimicrobial peptide; HAMP; putative liver tumor regressor; PLTR; liver-expressed antimicrobial peptide 1; LEAP-1) with potential use in the treatment of iron deficiency anemia and iron overload secondary to hematologic disorders. Upon administration, rusfertide mimics endogenous hepcidin, a protein primarily produced in hepatocytes, and increases hepcidin levels. As hepcidin plays a key role in the homeostasis of systemic iron, rusfertide may serve to normalize iron levels. Low levels of endogenous hepcidin are associated with iron overload secondary to excessive absorption of iron as seen in beta thalassemia and paradoxically with iron deficiency anemia.

1 2D Structure

Rusfertide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-5-[4-[(3S,6S,9S,12S,15R,20R,26S,29S,32S,35S)-26-(4-aminobutyl)-6-benzyl-12-[(2S)-butan-2-yl]-32-(3-carbamimidamidopropyl)-3-(2-carboxyethyl)-15-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-3-carboxy-2-(3-methylbutanoylamino)propanoyl]amino]-3-hydroxybutanoyl]amino]-3-(1H-imidazol-4-yl)propanoyl]amino]-3-phenylpropanoyl]pyrrolidine-2-carbonyl]amino]-20-[[(2S)-1,6-diamino-1-oxohexan-2-yl]carbamoyl]-29-(hydroxymethyl)-2,5,8,11,14,22,25,28,31,34-decaoxo-17,18-dithia-1,4,7,10,13,21,24,27,30,33-decazabicyclo[33.3.0]octatriacontan-9-yl]butylamino]-2-(hexadecanoylamino)-5-oxopentanoic acid

2.1.2 InChI

InChI=1S/C114H181N27O28S2/c1-7-9-10-11-12-13-14-15-16-17-18-19-26-46-90(145)125-79(113(168)169)47-49-89(144)121-53-32-29-42-76-99(154)133-80(58-71-36-22-20-23-37-71)101(156)132-78(48-50-93(148)149)111(166)140-55-34-44-87(140)107(162)130-77(43-33-54-122-114(118)119)100(155)136-84(64-142)104(159)129-75(41-28-31-52-116)98(153)123-63-92(147)127-85(105(160)128-74(97(117)152)40-27-30-51-115)65-170-171-66-86(106(161)138-95(69(5)8-2)109(164)131-76)137-108(163)88-45-35-56-141(88)112(167)83(59-72-38-24-21-25-39-72)135-102(157)81(60-73-62-120-67-124-73)134-110(165)96(70(6)143)139-103(158)82(61-94(150)151)126-91(146)57-68(3)4/h20-25,36-39,62,67-70,74-88,95-96,142-143H,7-19,26-35,40-61,63-66,115-116H2,1-6H3,(H2,117,152)(H,120,124)(H,121,144)(H,123,153)(H,125,145)(H,126,146)(H,127,147)(H,128,160)(H,129,159)(H,130,162)(H,131,164)(H,132,156)(H,133,154)(H,134,165)(H,135,157)(H,136,155)(H,137,163)(H,138,161)(H,139,158)(H,148,149)(H,150,151)(H,168,169)(H4,118,119,122)/t69-,70+,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,95-,96-/m0/s1

2.1.3 InChI Key

JRVOBXXOZFTSRF-GVIPULMVSA-N

2.1.4 Canonical SMILES

CCCCCCCCCCCCCCCC(=O)NC(CCC(=O)NCCCCC1C(=O)NC(C(=O)NC(C(=O)N2CCCC2C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(CSSCC(C(=O)NC(C(=O)N1)C(C)CC)NC(=O)C3CCCN3C(=O)C(CC4=CC=CC=C4)NC(=O)C(CC5=CNC=N5)NC(=O)C(C(C)O)NC(=O)C(CC(=O)O)NC(=O)CC(C)C)C(=O)NC(CCCCN)C(=O)N)CCCCN)CO)CCCNC(=N)N)CCC(=O)O)CC6=CC=CC=C6)C(=O)O

2.1.5 Isomeric SMILES

CCCCCCCCCCCCCCCC(=O)N[C@@H](CCC(=O)NCCCC[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N2CCC[C@H]2C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N1)[C@@H](C)CC)NC(=O)[C@@H]3CCCN3C(=O)[C@H](CC4=CC=CC=C4)NC(=O)[C@H](CC5=CNC=N5)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(=O)O)NC(=O)CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N)CCCCN)CO)CCCNC(=N)N)CCC(=O)O)CC6=CC=CC=C6)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

XM71MYX0IQ

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Rusfertide [usan]

2. Xm71myx0iq

3. Ptg-300fb

4. Ptg-300

5. 1628323-80-7

6. Isovaleryl-asp-thr-his-phe-pro-cyclo(cys-ile-lys(palm-gamma-glu)- Phe-glu-pro-arg-ser-lys-gly-cys)-lys-nh2

7. Rusfertide [inn]

8. Unii-xm71myx0iq

9. Who 11456

10. L-lysinamide, N-(3-methyl-1-oxobutyl)-l-.alpha.-aspartyl-l-threonyl-l-histidyl-l-phenylalanyl-l-prolyl-l-cysteinyl-l-isoleucyl-n6-(n-(1-oxohexadecyl)-l-.gamma.-glutamyl)-l-lysyl-l-phenylalanyl-l-.alpha.-glutamyl-l-prolyl-l-arginyl-l-seryl-l-lysylglycyl-l-cysteinyl-

11. N-(3-methyl-1-oxobutyl)-l-.alpha.-aspartyl-l-threonyl-l-histidyl-l-phenylalanyl-l-prolyl-l-cysteinyl-l-isoleucyl-n6-(n-(1-oxohexadecyl)-l-.gamma.-glutamyl)-l-lysyl-l-phenylalanyl-l-.alpha.-glutamyl-l-prolyl-l-arginyl-l-seryl-l-lysylglycyl-l-cysteinyl-l-lysinamide

2.4 Create Date

2021-04-15

3 Chemical and Physical Properties

Molecular Formula	C₁₁₄H₁₈₁N₂₇O₂₈S₂
Molecular Weight	2442.0 g/mol
XLogP3	-1.5
Hydrogen Bond Donor Count	29
Hydrogen Bond Acceptor Count	34
Rotatable Bond Count	67
Exact Mass	2441.3044354 g/mol
Monoisotopic Mass	2440.3010806 g/mol
Topological Polar Surface Area	924 Å²
Heavy Atom Count	171
Formal Charge	0
Complexity	5090
Isotope Atom Count	0
Defined Atom Stereocenter Count	19
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1