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2D Structure
Also known as: Sodium colistin methanesulfonate, Colistin sulfomethate, Colimycin m, 12705-41-8, Colistinmethanesulfonic acid, Sodium colistimethate
Molecular Formula
C58H105N16Na5O28S5
Molecular Weight
1749.8  g/mol
InChI Key
IQWHCHZFYPIVRV-UHFFFAOYSA-I

Colistimethate is a broad-spectrum polymyxin antibiotic against most aerobic Gram-negative bacteria except Proteus bacteria. Colistimethate is a mixture of methanesulfonate derivatives of cyclic polypeptides colistin A and B from Bacillus colistinus or B. polymyxa. Colistin functions as a surfactant which penetrates into and disrupts the bacterial cell membrane, thereby resulting in bactericidal effect.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
pentasodium;[2-[17-(1-hydroxyethyl)-22-[[2-[[3-hydroxy-2-[[2-(6-methyloctanoylamino)-4-(sulfonatomethylamino)butanoyl]amino]butanoyl]amino]-4-(sulfonatomethylamino)butanoyl]amino]-5,8-bis(2-methylpropyl)-3,6,9,12,15,18,23-heptaoxo-11,14-bis[2-(sulfonatomethylamino)ethyl]-1,4,7,10,13,16,19-heptazacyclotricos-2-yl]ethylamino]methanesulfonate
2.1.2 InChI
InChI=1S/C58H110N16O28S5.5Na/c1-9-35(6)12-10-11-13-46(77)65-38(14-20-59-28-103(88,89)90)53(82)74-48(37(8)76)58(87)70-41(17-23-62-31-106(97,98)99)50(79)68-43-19-25-64-57(86)47(36(7)75)73-54(83)42(18-24-63-32-107(100,101)102)67-49(78)39(15-21-60-29-104(91,92)93)69-55(84)44(26-33(2)3)72-56(85)45(27-34(4)5)71-52(81)40(66-51(43)80)16-22-61-30-105(94,95)96;;;;;/h33-45,47-48,59-63,75-76H,9-32H2,1-8H3,(H,64,86)(H,65,77)(H,66,80)(H,67,78)(H,68,79)(H,69,84)(H,70,87)(H,71,81)(H,72,85)(H,73,83)(H,74,82)(H,88,89,90)(H,91,92,93)(H,94,95,96)(H,97,98,99)(H,100,101,102);;;;;/q;5*+1/p-5
2.1.3 InChI Key
IQWHCHZFYPIVRV-UHFFFAOYSA-I
2.1.4 Canonical SMILES
CCC(C)CCCCC(=O)NC(CCNCS(=O)(=O)[O-])C(=O)NC(C(C)O)C(=O)NC(CCNCS(=O)(=O)[O-])C(=O)NC1CCNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)CCNCS(=O)(=O)[O-])CC(C)C)CC(C)C)CCNCS(=O)(=O)[O-])CCNCS(=O)(=O)[O-])C(C)O.[Na+].[Na+].[Na+].[Na+].[Na+]
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Colistimethate Sodium

2. Colistimethate, Disodium Salt

3. Colistin Sodium Methanesulfonate

4. Colistinmethanesulfonic Acid

2.2.2 Depositor-Supplied Synonyms

1. Sodium Colistin Methanesulfonate

2. Colistin Sulfomethate

3. Colimycin M

4. 12705-41-8

5. Colistinmethanesulfonic Acid

6. Sodium Colistimethate

7. Colistrimethate Sodium

8. Colymycin M

9. Coly-mycin M

10. Colimyscine

11. Colimicina

12. Coly-mycin Injectable

13. Colistin Sulfomethate Sodium

14. Coly-mycin M Parenteral

15. Sodium Colistinemethanesulfonate

16. Colistinemethanesulfonate Sodique

17. Pentasodium Colistinmethanesulfonate

18. Pentasodium;[2-[17-(1-hydroxyethyl)-22-[[2-[[3-hydroxy-2-[[2-(6-methyloctanoylamino)-4-(sulfonatomethylamino)butanoyl]amino]butanoyl]amino]-4-(sulfonatomethylamino)butanoyl]amino]-5,8-bis(2-methylpropyl)-3,6,9,12,15,18,23-heptaoxo-11,14-bis[2-(sulfonatomethylamino)ethyl]-1,4,7,10,13,16,19-heptazacyclotricos-2-yl]ethylamino]methanesulfonate

19. Einecs 232-516-9

20. Unii-xw0e5ys77g

21. Colistinmethanesulfonic Acid, Sodium Salt

22. 8068-37-9

23. Colistimethate Sodium [usan:usp:inn:ban]

24. Xw0e5ys77g

25. Unii-dl2r53p963

26. Dl2r53p963

27. Colistinmethanesulfonic Acid (van)

28. Nsc 756688

29. Sw222239-1

2.3 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 1749.8 g/mol
Molecular Formula C58H105N16Na5O28S5
Hydrogen Bond Donor Count18
Hydrogen Bond Acceptor Count33
Rotatable Bond Count39
Exact Mass1748.5376240 g/mol
Monoisotopic Mass1748.5376240 g/mol
Topological Polar Surface Area749 Ų
Heavy Atom Count112
Formal Charge0
Complexity3430
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count13
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count6
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameColistimethate sodium
PubMed HealthColistimethate (Injection)
Drug ClassesAntibiotic
Drug LabelColistimethate for Injection, USP is a sterile parenteral antibiotic product which, when reconstituted (see Reconstitution), is suitable for intramuscular or intravenous administration.Each vial contains colistimethate sodium or pentasodium colistinm...
Active IngredientColistimethate sodium
Dosage FormInjectable
RouteInjection
Strengtheq 150mg base/vial
Market StatusPrescription
CompanyEmcure Pharms; Fresenius Kabi Usa; Paddock; X Gen Pharms; Sagent Pharms

2 of 4  
Drug NameColy-mycin m
Drug LabelColy-Mycin M Parenteral (Colistimethate for Injection, USP) is a sterile parenteral antibiotic product which, when reconstituted (see Reconstitution), is suitable for intramuscular or intravenous administration.Each vial contains colistimethate sod...
Active IngredientColistimethate sodium
Dosage FormInjectable
RouteInjection
Strengtheq 150mg base/vial
Market StatusPrescription
CompanyPar Sterile Products

3 of 4  
Drug NameColistimethate sodium
PubMed HealthColistimethate (Injection)
Drug ClassesAntibiotic
Drug LabelColistimethate for Injection, USP is a sterile parenteral antibiotic product which, when reconstituted (see Reconstitution), is suitable for intramuscular or intravenous administration.Each vial contains colistimethate sodium or pentasodium colistinm...
Active IngredientColistimethate sodium
Dosage FormInjectable
RouteInjection
Strengtheq 150mg base/vial
Market StatusPrescription
CompanyEmcure Pharms; Fresenius Kabi Usa; Paddock; X Gen Pharms; Sagent Pharms

4 of 4  
Drug NameColy-mycin m
Drug LabelColy-Mycin M Parenteral (Colistimethate for Injection, USP) is a sterile parenteral antibiotic product which, when reconstituted (see Reconstitution), is suitable for intramuscular or intravenous administration.Each vial contains colistimethate sod...
Active IngredientColistimethate sodium
Dosage FormInjectable
RouteInjection
Strengtheq 150mg base/vial
Market StatusPrescription
CompanyPar Sterile Products

5 Pharmacology and Biochemistry
5.1 FDA Pharmacological Classification
5.1.1 Pharmacological Classes
Polymyxins [CS]; Polymyxin-class Antibacterial [EPC]