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Substance Name: Netilmicin sulfate [USAN:USP:JAN]
RN: 56391-57-2
UNII: S741ZJS97U
InChIKey: AGFWIZQEWFGATK-UNZHCMSXSA-N

Note

  • Semisynthetic 1-N-ethyl derivative of SISOMYCIN, an aminoglycoside antibiotic with action similar to gentamicin, but less ear and kidney toxicity.

Molecular Formula

  • C21-H41-N5-O7.5/2H2-O4-S

Molecular Weight

  • 1441.55
 

Classification Codes

  • Antibacterial
  • Drug / Therapeutic Agent
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Netilmicin sulfate
  • Netilmicin sulfate [USAN:USP:JAN]

Synonyms

  • Certomycin
  • D-Streptamine, O-3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1-4))-2-deoxy-N(sup 1)-ethyl-, sulfate (2:5) (salt)
  • EINECS 260-147-3
  • Netillin
  • Netilmicin sulfate
  • Netromycin
  • Nettacin
  • NTL sulfate
  • O-3-Deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-4)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1-6))-2-deoxy-N(sup 3)-ethyl-L-streptamine sulfate (2:5) (salt)
  • O-3-Deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1->4)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1->6))-2-deoxy-N(sup 3)-ethyl-L-streptamine sulfate (2:5) (salt)
  • Sch 20569
  • UNII-S741ZJS97U
  • Zetamicin

Systematic Names

  • D-Streptamine, O-3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1->6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1->4))-2-deoxy-N(sup 1)-ethyl-, sulfate (2:5) (salt)
  • d-Streptamine, O-3-deoxy-4-C-methyl-3-(methylamino)-beta-l-arabinopyranosyl-(1.6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1.4))-2-deoxy-N1-ethyl-, sulfate (2:5) (salt)
  • D-Streptamine, O-3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1.fwdarw.6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1.fwdarw.4))-2-deoxy-N1-ethyl-, sulfate (2:5) (salt)

Superlist Name

  • Netilmicin sulfate

Registry Numbers

CAS Registry Number

  • 56391-57-2

FDA UNII

  • S741ZJS97U

Related Registry Number

  • 56391-56-1 (Parent)

System Generated Number

  • 0056391572

Molecular Formulas

Molecular Formula

  • C21-H41-N5-O7.5/2H2-O4-S

Molecular Formula Fragments

  • C21-H41-N5-O7
  • COMPONENT
  • H2-O4-S

Structure Descriptors

InChI

1S/2C21H41N5O7.5H2O4S/c2*1-4-26-13-7-12(24)16(32-19-11(23)6-5-10(8-22)31-19)14(27)17(13)33-20-15(28)18(25-3)21(2,29)9-30-20;5*1-5(2,3)4/h2*5,11-20,25-29H,4,6-9,22-24H2,1-3H3;5*(H2,1,2,3,4)/t2*11-,12+,13-,14+,15-,16-,17+,18-,19-,20-,21+;;;;;/m11...../s1

InChIKey

AGFWIZQEWFGATK-UNZHCMSXSA-N

Smiles

O([C@H]1[C@@H](C[C@@H]([C@H]([C@@H]1O)O[C@H]1OC(=CC[C@H]1N)CN)N)NCC)[C@@H]1[C@@H]([C@@H](NC)[C@@](C)(O)CO1)O.S(O)(O)(=O)=O.O([C@H]1[C@@H](C[C@H](N)[C@H]([C@@H]1O)O[C@H]1OC(=CC[C@H]1N)CN)NCC)[C@@H]1[C@@H]([C@H]([C@@](C)(O)CO1)NC)O.S(O)(O)(=O)=O.S(O)(O)(=O)=O.S(O)(O)(=O)=O.S(O)(O)(=O)=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intramuscular 63100ug/kg (63.1mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Japanese Journal of Antibiotics. Vol. 35, Pg. 461, 1982.
mouse LD50 intraperitoneal 189mg/kg (189mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) Antimicrobial Agents and Chemotherapy. Vol. 10, Pg. 827, 1976.
mouse LD50 intravenous 22mg/kg (22mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE
Japanese Journal of Antibiotics. Vol. 35, Pg. 461, 1982.
mouse LD50 subcutaneous 68900ug/kg (68.9mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: ATAXIA
Japanese Journal of Antibiotics. Vol. 35, Pg. 461, 1982.
rat LD50 intramuscular 167mg/kg (167mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Japanese Journal of Antibiotics. Vol. 35, Pg. 461, 1982.
rat LD50 intraperitoneal 231mg/kg (231mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: ATAXIA
Japanese Journal of Antibiotics. Vol. 35, Pg. 461, 1982.
rat LD50 intravenous 40700ug/kg (40.7mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Japanese Journal of Antibiotics. Vol. 35, Pg. 461, 1982.
rat LD50 oral > 10gm/kg (10000mg/kg)   Yakkyoku. Pharmacy. Vol. 36, Pg. 1249, 1985.
rat LD50 subcutaneous 169mg/kg (169mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Japanese Journal of Antibiotics. Vol. 35, Pg. 461, 1982.