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Also known as: Mocravimod, Krp-203 free base, 509092-16-4, X71gcj0hli, 2-amino-2-(4-((3-(benzyloxy)phenyl)thio)-2-chlorophenethyl)propane-1,3-diol, 1,3-propanediol, 2-amino-2-(2-(2-chloro-4-((3-(phenylmethoxy)phenyl)thio)phenyl)ethyl)-

Molecular Formula

C₂₄H₂₆ClNO₃S

Molecular Weight

444.0 g/mol

InChI Key

IINUNQPYJGJCJI-UHFFFAOYSA-N

FDA UNII

X71GCJ0HLI

Mocravimod is a sphingosine 1-phosphate (S1P) receptor agonist, with potential immunosuppressive activity. Upon administration of mocravimod, this agent binds to S1P receptors on lymphocytes, which prevents binding of serum S1P to S1P receptors and leads to S1P receptor internalization. This reduces the number of circulating blood leukocytes and accelerates lymphocyte homing into peripheral lymph nodes, thereby preventing their infiltration into peripheral inflammatory sites. This agent also decreases the production of inflammatory cytokines by lymphocytes, such as interferon gamma (IFN-g), interleukin-12 (IL-12), and tumor necrosis factor (TNF).

1 2D Structure

Mocravimod

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-amino-2-[2-[2-chloro-4-(3-phenylmethoxyphenyl)sulfanylphenyl]ethyl]propane-1,3-diol

2.1.2 InChI

InChI=1S/C24H26ClNO3S/c25-23-14-22(10-9-19(23)11-12-24(26,16-27)17-28)30-21-8-4-7-20(13-21)29-15-18-5-2-1-3-6-18/h1-10,13-14,27-28H,11-12,15-17,26H2

2.1.3 InChI Key

IINUNQPYJGJCJI-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC=C(C=C1)COC2=CC(=CC=C2)SC3=CC(=C(C=C3)CCC(CO)(CO)N)Cl

2.2 Other Identifiers

2.2.1 UNII

X71GCJ0HLI

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Mocravimod

2. Krp-203 Free Base

3. 509092-16-4

4. X71gcj0hli

5. 2-amino-2-(4-((3-(benzyloxy)phenyl)thio)-2-chlorophenethyl)propane-1,3-diol

6. 1,3-propanediol, 2-amino-2-(2-(2-chloro-4-((3-(phenylmethoxy)phenyl)thio)phenyl)ethyl)-

7. Unii-x71gcj0hli

8. Mocravimod [inn]

9. Mocravimod [who-dd]

10. Schembl641641

11. Gtpl9727

12. Krp203

13. Chembl2137148

14. Dtxsid30965173

15. Zinc6744940

16. Compound 2 [pmid: 23124563]

17. Ncgc00250388-01

18. Q27293620

19. 2-amino-2-[2-(4-{[3-(benzyloxy)phenyl]sulfanyl}-2-chlorophenyl)ethyl]propane-1,3-diol

20. 2-amino-2-[2-[2-chloro-4-(3-phenylmethoxyphenyl)sulfanylphenyl]ethyl]propane-1,3-diol

21. 2-amino-2-[2-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]ethyl]-1,3-propanediol

2.4 Create Date

2006-10-26

3 Chemical and Physical Properties

Molecular Formula	C₂₄H₂₆ClNO₃S
Molecular Weight	444.0 g/mol
XLogP3	4.3
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	10
Exact Mass	443.1321926 g/mol
Monoisotopic Mass	443.1321926 g/mol
Topological Polar Surface Area	101 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	487
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1