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2058-46-0

2058-46-0 structure
2058-46-0 structure
  • Name: Oxytetracycline HCl
  • Chemical Name: oxytetracycline hydrochloride
  • CAS Number: 2058-46-0
  • Molecular Formula: C22H25ClN2O9
  • Molecular Weight: 533.356
  • Catalog: API Antibiotics Tetracycline
  • Create Date: 2018-02-06 08:00:00
  • Modify Date: 2024-01-02 18:27:44
  • Oxytetracycline hydrochloride is an antibiotic belonging to the tetracycline class. Oxytetracycline hydrochloride potent inhibits Gram-negative and Gram-positive bacteria. Oxytetracycline hydrochloride is a protein synthesis inhibitor and prevents the binding from aminoacil-tRNA to the complex m-ribosomal RNA. Oxytetracycline hydrochloride also possesses anti-HSV-1 activity[1][2][3].
Name oxytetracycline hydrochloride
Synonyms engemycin
mepatar
Oxytetracycline Hydrochloride
MFCD00135815
oxytetracyclin hydrochloride
(4S,4aR,5S,5aR,6S,12aS)-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide hydrochloride (1:1)
oxlopar
EINECS 218-161-2
Oxytetracycline Hydrochloride,Can be Used as Secondary Standard
oxytetracycline HCl
Oxycline
terramycin hydrochloride
(4S,4aR,5S,5aR,6S,12aS)-4-dimethylamino-1,4,4a,5,5a,6,11,12a-octahydro-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxonaphthacene-2-carboxamide hydrochloride
otetryn
TOXINAL
GEOMYCIN
tm5
OTC
Description Oxytetracycline hydrochloride is an antibiotic belonging to the tetracycline class. Oxytetracycline hydrochloride potent inhibits Gram-negative and Gram-positive bacteria. Oxytetracycline hydrochloride is a protein synthesis inhibitor and prevents the binding from aminoacil-tRNA to the complex m-ribosomal RNA. Oxytetracycline hydrochloride also possesses anti-HSV-1 activity[1][2][3].
Related Catalog
Target

Gram-negative and Gram-positive bacteria[1] HSV-1[3]

In Vitro Oxytetracycline is an important member of the bacterial aromatic polyketide family, which is a structurally diverse class of natural products. Oxytetracycline is synthesized by a type II polyketide synthase that generates the poly-beta-ketone backbone through successive decarboxylative condensation of malonyl-CoA extender units, followed by modifications by cyclases, oxygenases, transferases, and additional tailoring enzymes[2].
In Vivo The effects of administration a therapeutic dose of Oxytetracycline (82.8 mg/kg of bw to 1 % bw/day) for 10 days are species specific. Oxytetracycline increases the relative liver weight in Morone chrysops x M. saxatilis, the enzymatic activity of CYP3A4 in Ictalurus punctatus, protein expression of CYP3A4 in Oreochromis niloticus and depleted the hepatic CYP3A4 in the latter[1]. For Oxytetracycline, the limits are 100 μg/kg in muscle and milk, 200 μg/kg in egg, 300 μg/kg in liver and 600 μg/kg in kidney. Oxytetracycline (OTC) is administered to fish as medicated feed at concentrations ranging from 35 to 75 mg a.i kg-1 biomass day-1 for 7-14 days[1].
References

[1]. Elia AC, et al. Transferability of oxytetracycline (OTC) from feed to carp muscle and evaluation of the antibiotic effects on antioxidant systems in liver and kidney. Fish Physiol Biochem. 2014 Aug;40(4):1055-68.

[2]. Pickens LB, et al. Oxytetracycline biosynthesis. J Biol Chem. 2010 Sep 3;285(36):27509-15.

[3]. Oguz Guvenmez, et al. A New Treatment Method for Herpes Simplex Virus Type 1-related Skin Lesions. Scientific & Academic. 2019; 8(1): 6-8.
Density 1.71 g/cm3
Boiling Point 839.6ºC at 760 mmHg
Melting Point 180°C
Molecular Formula C22H25ClN2O9
Molecular Weight 533.356
Flash Point 461.6ºC
Exact Mass 532.101563
PSA 201.85000
LogP 0.25870
Vapour Pressure 2.17E-30mmHg at 25°C
Storage condition 0-6°C
Water Solubility >100 g/L

CHEMICAL IDENTIFICATION

RTECS NUMBER :
QI8225000
CHEMICAL NAME :
2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5, 6,10,12,12a- hexahydroxy-6-methyl-1,11-dioxo-, monohydrochloride
CAS REGISTRY NUMBER :
2058-46-0
LAST UPDATED :
199701
DATA ITEMS CITED :
26
MOLECULAR FORMULA :
C22-H24-N2-O9.Cl-H
MOLECULAR WEIGHT :
496.94
WISWESSER LINE NOTATION :
L E6 C666 BV FV CU GUTTT&J DQ EQ GVZ HQ IN1&1 KQ MQ M1 RQ &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
800 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
302 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
6696 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
600 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
100 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
100 mg/kg
TOXIC EFFECTS :
Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
80 mg/kg
TOXIC EFFECTS :
Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Behavioral - excitement
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1802 gm/kg/2Y
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Endocrine - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Parenteral
DOSE :
20 mg/kg
SEX/DURATION :
female 20 week(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - abortion
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
11250 mg/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
12 gm/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
21 gm/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - uterus, cervix, vagina
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
900 mg/kg
SEX/DURATION :
female 10-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
TYPE OF TEST :
Micronucleus test

MUTATION DATA

TYPE OF TEST :
Unscheduled DNA synthesis
TEST SYSTEM :
Mammal - species unspecified Lymphocyte
DOSE/DURATION :
20 mg/L
REFERENCE :
BIORAK Biochemistry (English Translation). Translation of BIOHAO. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) V.21- 1956- Volume(issue)/page/year: 39,587,1974 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 83236 No. of Facilities: 49 (estimated) No. of Industries: 2 No. of Occupations: 6 No. of Employees: 9441 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 83236 No. of Facilities: 763 (estimated) No. of Industries: 2 No. of Occupations: 10 No. of Employees: 20845 (estimated) No. of Female Employees: 16524 (estimated)
Symbol GHS08
GHS08
Signal Word Warning
Hazard Statements H361d
Precautionary Statements P281
Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xn:Harmful
Risk Phrases R36;R63
Safety Phrases S36/37/39-S26
RIDADR NONH for all modes of transport
WGK Germany 2
RTECS QI8225000
HS Code 3003209000
61068-97-1 structure

61068-97-1

~79%

2058-46-0 structure

2058-46-0

Literature: Issar, M. M.; Mahadevan, P. R. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1981 , vol. 20, # 3 p. 257 - 258
Precursor  1

DownStream  0

HS Code 3003209000

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