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Basic Information
CAS No.: 57-62-5
Name: Chlorotetracycline
Molecular Structure:
Molecular Structure of 57-62-5 (Chlorotetracycline)
Formula: C22H23ClN2O8
Molecular Weight: 478.886
Synonyms: 2-Naphthacenecarboxamide,7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-(7CI,8CI);2-Naphthacenecarboxamide,7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-,[4S-(4a,4aa,5aa,6b,12aa)]-;Aureomicina;Aureomycin;Aureomykoin;Aurofac;Aureocina;A-Mycin;Acronize;7-Chlorotetracycline;7-Chlortetracycline;Tri-chlortetracycline;Acronize PD;Chrysomykine;Chlortetracycline;Centraureo;Chlorocyclinum;
EINECS: 200-341-7
Density: 1.7 g/cm3
Melting Point: 168.5oC
Boiling Point: 821.078 °C at 760 mmHg
Flash Point: 450.372 °C
Solubility: 0.63g/L(25 oC)
Appearance: Golden yellow crystal powder
Hazard Symbols: HarmfulXn
Risk Codes: 22
PSA: 181.62000
LogP: 1.13930
Synthetic route
67-56-1

methanol

14297-93-9

4-epi chlortetracycline

NaH2PO4

NaH2PO4

57-62-5

Chlortetracycline

Conditions
ConditionsYield
Gleichgeweicht;
57-62-5

Chlortetracycline

A

C20H16ClNO9

B

4-(((1S,4R,10S)-9-chloro-6-hydroxy-1-methyl-3,5-dioxo-1,3,4,5-tetrahydro-1,4-methanobenzo[c]oxepin-10-yl)methyl)-2,3,5,6-tetrahydroxybenzamide

Conditions
ConditionsYield
With mercury(II) diacetate; magnesium sulfate; acetic acid; sodium hydroxide In tetrahydrofuran at 50℃; for 48h;A 17.5%
B 34%
57-62-5

Chlortetracycline

514-53-4

isochlortetracycline

Conditions
ConditionsYield
With sodium hydroxide
With potassium hydroxide
57-62-5

Chlortetracycline

3811-34-5, 66749-14-2, 66749-15-3

(S)-4-((1S)-4-carbamoyl-2t-dimethylamino-3,6ξ-dihydroxy-5-oxo-cyclohex3-en-r-yl)-3-((S)-7-chloro-4-hydroxy-1-methyl-3-oxo-phthalan-1-yl)-butyric acid

Conditions
ConditionsYield
With sodium hydroxide; sodium dithionite β-aureomycinic acid;
With sodium hydroxide; sodium dithionite α-aureomycinic acid;
With sodium hydroxide; zinc β-aureomycinic acid;
57-62-5

Chlortetracycline

1885-13-8

4-methoxyphthalic acid

Conditions
ConditionsYield
Behandeln des Reaktionsprodukts mit KMnO4;
57-62-5

Chlortetracycline

60-54-8

TETRACYCLINE

Conditions
ConditionsYield
With palladium on activated charcoal; 2-methoxy-ethanol; triethylamine Hydrogenation;
With 1,4-dioxane; methanol; palladium on activated charcoal Hydrogenation;
57-62-5

Chlortetracycline

1665-56-1, 7518-17-4

anhydrotetracycline

Conditions
ConditionsYield
With hydrogen iodide
57-62-5

Chlortetracycline

4497-08-9

(4S,4aS,12aS)-7-chloro-4-(dimethylamino)-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-1,4,4a,5,12,12a-hexahydrotetracene-2-carboxamide

Conditions
ConditionsYield
With hydrogenchloride
57-62-5

Chlortetracycline

14297-93-9

4-epi chlortetracycline

Conditions
ConditionsYield
With sodium dihydrogenphosphate; N,N-dimethyl-formamide
57-62-5

Chlortetracycline

3811-33-4, 66749-13-1

(S)-4-(4-carbamoyl-2,3,5-trihydroxy-phenyl)-3-((S)-7-chloro-4-hydroxy-1-methyl-3-oxo-phthalan-1-yl)-butyric acid

Conditions
ConditionsYield
With sodium hydroxide
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Specification

The Chlortetracycline, with the CAS registry number 57-62-5, is also known as 7-Chlorotetracycline. It belongs to the product categories of Pharmaceuticals. Its EINECS registry number is 200-341-7. This chemical's molecular formula is C22H23ClN2O8 and molecular weight is 478.88. Its IUPAC name is called (4S,4αS,5αS,6S,12αS,Z)-2-[amino(hydroxy)methylene]-7-chloro-4-(dimethylamino)-6,10,11,12α-tetrahydroxy-6-methyl-4α,5,5α,6-tetrahydrotetracene-1,3,12(2H,4H,12αH)-trione. This chemical's classification codes are Agricultural Chemical; Anti-Bacterial Agents; Anti-Infective Agents; Antibacterial; Antiparasitic Agents; Antiprotozoal; Antiprotozoal agents; Drug / Therapeutic Agent; Enzyme Inhibitors; Fungicide, bactericide, wood preservative; Protein Synthesis Inhibitors; Reproductive Effect. When you are using this chemical, please be cautious about it. This chemical may cause damage to health. It is harmful if swallowed.

Physical properties of Chlortetracycline: (1)ACD/LogP: 1.32; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): -3; (4)ACD/LogD (pH 7.4): -4; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 10; (10)#H bond donors: 7; (11)#Freely Rotating Bonds: 7; (12)Index of Refraction: 1.745; (13)Molar Refractivity: 113.915 cm3; (14)Molar Volume: 281.089 cm3; (15)Surface Tension: 101.962 dyne/cm; (16)Density: 1.704 g/cm3; (17)Flash Point: 450.372 °C; (18)Enthalpy of Vaporization: 125.108 kJ/mol; (19)Boiling Point: 821.078 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.

Preparation: this chemical can be prepared by Streptomyces (Streptomyces aureofacieus). This reaction will need solvent ethanol.

Chlortetracycline (trade name Aureomycin, Lederle) is a tetracycline antibiotic, and was the first tetracycline to be discovered. In veterinary medicine, it is commonly used to treat conjunctivitis in cats. What's more, this chemical can be used to inhibit gram-positive and electronegative bacterium, can treat typhoid, white scour and other diseases. It also can be used as promoting growth agent.

You can still convert the following datas into molecular structure:
(1)SMILES: CN(C)[C@@H]2C(\O)=C(\C(N)=O)C(=O)[C@@]3(O)C(/O)=C4/C(=O)c1c(O)ccc(Cl)c1[C@@](C)(O)[C@H]4C[C@@H]23
(2)InChI: InChI=1/C22H23ClN2O8/c1-21(32)7-6-8-15(25(2)3)17(28)13(20(24)31)19(30)22(8,33)18(29)11(7)16(27)12-10(26)5-4-9(23)14(12)21/h4-5,7-8,15,26,28-29,32-33H,6H2,1-3H3,(H2,24,31)/t7-,8-,15-,21-,22-/m0/s1
(3)InChIKey: CYDMQBQPVICBEU-XRNKAMNCBT

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 150mg/kg (150mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 52, 1959.
dog LD50 oral 750mg/kg (750mg/kg)   Antimicrobial Agents Annual. Vol. -, Pg. 595, 1960.
guinea pig LDLo intraperitoneal 1800mg/kg (1800mg/kg)   Antibiotiki. Vol. 20, Pg. 793, 1975.
mouse LD50 intracrebral 48mg/kg (48mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: EXCITEMENT

MUSCULOSKELETAL: CHANGES IN TEETH AND SUPPORTING STRUCTURES
Chemotherapy Vol. 26, Pg. 196, 1980.
mouse LD50 intravenous 134mg/kg (134mg/kg)   Antibiotics and Chemotherapy Vol. 6, Pg. 623, 1956.
mouse LD50 oral 1500mg/kg (1500mg/kg)   Antimicrobial Agents Annual. Vol. -, Pg. 595, 1960.
mouse LDLo intraperitoneal 192mg/kg (192mg/kg)   Compilation of LD50 Values of New Drugs.
mouse LDLo subcutaneous 3gm/kg (3000mg/kg)   Antibiotics and Chemotherapy Vol. 6, Pg. 623, 1956.
rat LD50 intravenous 118mg/kg (118mg/kg)   Antibiotics and Chemotherapy Vol. 6, Pg. 623, 1956.
rat LDLo intraperitoneal 335mg/kg (335mg/kg)   Compilation of LD50 Values of New Drugs.
rat LDLo oral 3gm/kg (3000mg/kg)   Journal of Agricultural and Food Chemistry. Vol. 17, Pg. 497, 1969.