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Chemistry

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Also known as: Cem-101, Solithera, 760981-83-7, Op-1068, Cem 101, Op 1068

Molecular Formula

C₄₃H₆₅FN₆O₁₀

Molecular Weight

845.0 g/mol

InChI Key

IXXFZUPTQVDPPK-ZAWHAJPISA-N

FDA UNII

9U1ETH79CK

Solithromycin is a ketolide antibiotic undergoing clinical development for the treatment of community-acquired pneumonia (CAP) and other infections.

1 2D Structure

Solithromycin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1S,2R,5S,7R,8R,9R,11R,13R,14R)-15-[4-[4-(3-aminophenyl)triazol-1-yl]butyl]-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-5-fluoro-9-methoxy-1,5,7,9,11,13-hexamethyl-3,17-dioxa-15-azabicyclo[12.3.0]heptadecane-4,6,12,16-tetrone

2.1.2 InChI

InChI=1S/C43H65FN6O10/c1-12-32-43(8)35(50(40(55)60-43)19-14-13-18-49-23-30(46-47-49)28-16-15-17-29(45)21-28)26(4)33(51)24(2)22-41(6,56-11)37(27(5)36(53)42(7,44)39(54)58-32)59-38-34(52)31(48(9)10)20-25(3)57-38/h15-17,21,23-27,31-32,34-35,37-38,52H,12-14,18-20,22,45H2,1-11H3/t24-,25-,26+,27+,31+,32-,34-,35-,37-,38+,41-,42+,43-/m1/s1

2.1.3 InChI Key

IXXFZUPTQVDPPK-ZAWHAJPISA-N

2.1.4 Canonical SMILES

CCC1C2(C(C(C(=O)C(CC(C(C(C(=O)C(C(=O)O1)(C)F)C)OC3C(C(CC(O3)C)N(C)C)O)(C)OC)C)C)N(C(=O)O2)CCCCN4C=C(N=N4)C5=CC(=CC=C5)N)C

2.1.5 Isomeric SMILES

CC[C@@H]1[C@@]2([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H](C(=O)[C@](C(=O)O1)(C)F)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)OC)C)C)N(C(=O)O2)CCCCN4C=C(N=N4)C5=CC(=CC=C5)N)C

2.2 Other Identifiers

2.2.1 UNII

9U1ETH79CK

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (3ar,4r,7s,9r,10r,11r,13r,15r,15ar)-1-(4-(4-(3-aminophenyl)-1h-1,2,3-triazol-1-yl)butyl)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyl-10-trideoxy-(dimethylamino)-

2. Cem 101

3. Cem-101

4. Op 1068

5. Op-1068

2.3.2 Depositor-Supplied Synonyms

1. Cem-101

2. Solithera

3. 760981-83-7

4. Op-1068

5. Cem 101

6. Op 1068

7. 9u1eth79ck

8. (1s,2r,5s,7r,8r,9r,11r,13r,14r)-15-[4-[4-(3-aminophenyl)triazol-1-yl]butyl]-8-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-5-fluoro-9-methoxy-1,5,7,9,11,13-hexamethyl-3,17-dioxa-15-azabicyclo[12.3.0]heptadecane-4,6,12,16-tetrone

9. (3as,4r,7s,9r,10r,11r,13r,15r,15ar)-1-{4-[4-(3-aminophenyl)-1h-1,2,3-triazol-1-yl]butyl}-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6,8,14-tetraoxotetradecahydro-2h-oxacyclotetradecino[4,3-d][1,3]oxazol-10-yl 3,4,6-trideoxy-3-(dimethylamino)-beta-d-xylo-hexopyranoside

10. Solithromycin [usan]

11. Unii-9u1eth79ck

12. Solithromycin [usan:inn]

13. Solithromycin [inn]

14. Solithromycin [jan]

15. Solithromycin [who-dd]

16. Cem101

17. Chembl1232510

18. Schembl19114493

19. Gtpl10859

20. Dtxsid501028410

21. Ex-a2272

22. Opt-1068

23. Op1068

24. Zinc95627834

25. Akos032947334

26. Compound 3 [pmid: 30258539]

27. Cs-5053

28. Db09308

29. Solithromycin; Cem-101; Op-1068

30. Hy-17593

31. T4288

32. T-4288

33. A865552

34. Q7558263

35. (1r,2r,4r,6r,7r,8r,10s,13r,14s)-17-[4-[4-(3-aminophenyl)triazol-1-yl]butyl]-7-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-13-ethyl-10-fluoro-6-methoxy-2,4,6,8,10,14-hexamethyl-12,15-dioxa-17-azabicyclo[12.3.0]heptadecane-3,9,11,16-tetrone

36. (3ar,4r,7s,9r,10r,11r,13r,15r,15ar)-1-(4-(4-(3-aminophenyl)-1h-1,2,3-triazol-1-yl)butyl)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyl-10-((trideoxy-(dimethylamino)-

37. (3as,4r,7s,9r,10r,11r,13r,15r,15ar)-1-{4-[4-(3-aminophenyl)-1h-1,2,3-triazol-1-yl]butyl}-4-ethyl-7-fluoro-11-methoxy-3a

38. 2h-oxacyclotetradecino(4,3-d)oxazole-2,6,8,14(1h,7h,9h)-tetrone, 1-(4-(4-(3-aminophenyl)-1h-1,2,3-triazol-1-yl)butyl)-4-ethyl-7- Fluorooctahydro-11-methoxy-3a,7,9,11,13,15-hexamethyl-10-((3,4,6-trideoxy-3-(dimethylamino)-beta-d-xylo-hexopyranosyl)oxy)-, (3as,4r,7s,9r,10r,11r,13r,15r,15ar)-

39. Em1

2.4 Create Date

2009-05-11

3 Chemical and Physical Properties

Molecular Formula	C₄₃H₆₅FN₆O₁₀
Molecular Weight	845.0 g/mol
XLogP3	4.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	15
Rotatable Bond Count	11
Exact Mass	844.47462045 g/mol
Monoisotopic Mass	844.47462045 g/mol
Topological Polar Surface Area	198 Å²
Heavy Atom Count	60
Formal Charge	0
Complexity	1530
Isotope Atom Count	0
Defined Atom Stereocenter Count	13
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Investigated for the treatment of community-acquired pneumonia (CAP).

Treatment of gonococcal infection

Treatment of anthrax, Treatment of tularaemia, Treatment of bacterial pneumonia

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

5.2 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01F - Macrolides, lincosamides and streptogramins

J01FA - Macrolides

J01FA16 - Solithromycin

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Solithromycin

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