Name: Oxytetracycline
SKU: 79-57-2

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Basic Information

Molecular Structure:
CAS No.:	79-57-2
Name:	Oxytetracycline

Formula:	C₂₂H₂₄N₂O₉
Molecular Weight:	460.441
Synonyms:	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-(7CI,8CI);5-Hydroxytetracycline;Abbocin;Antibiotic TM 25;Biostat;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-,(4S,4aR,5S,5aR,6S,12aS)-;Dabicycline;Geomycin;Geomycin (Streptomyces vimosus);Geotilin;LA 200;Lenocycline;Liquamycin LA 200;Mycoshield TMQTHC 20;NSC 9169;Oxiter 200;Oxitetracyclin;Oxycline;Oxydon;Oxylim;Oxymykoin;Oxysentin 100;Oxyterracin;Oxyterracine;Oxytetracycline amphoteric;Oxytetral;Ryomycin;Stevacin;Stevasin;Tarosin;Terrafungine;Terralon LA;Terramycin343;Terramycin Q 50;Tetran;Ursocyclin;Ursocycline;Vendarcin;
EINECS:	201-212-8
Density:	1.71 g/cm³
Melting Point:	183 °C
Boiling Point:	727.8 °C at 760 mmHg
Flash Point:	394 °C
Solubility:	Slightly soluble in ethanol, very slightly soluble in water
Appearance:	beige to light yellow crystalline powder
Hazard Symbols:	Xn,Xi
Risk Codes:	63-36/37/38
Safety:	22-24/25-36/37/39-26
PSA:	201.85000
LogP:	-0.54330

Synthetic route

: 60-54-8
TETRACYCLINE

A: 79-57-2
Oxytetracycline

B: 1665-56-1, 7518-17-4
anhydrotetracycline

Conditions

Conditions	Yield
With laccase from Trametes versicolor In water at 25℃; for 24h; pH=6; Catalytic behavior; Kinetics; Reagent/catalyst; pH-value; Enzymatic reaction;

: 60-54-8
TETRACYCLINE

: 79-57-2
Oxytetracycline

Conditions

Conditions	Yield
With laccase from Pycnoporus sp. SYBC-L10; 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt In aq. phosphate buffer at 25℃; for 0.0666667h; pH=6; Catalytic behavior; Reagent/catalyst; Temperature; pH-value; Enzymatic reaction;

: 79-57-2
Oxytetracycline

: 108-24-7
acetic anhydride

: (5S,5aR,6S,6aR,7S,10aS)-9-carbamoyl-7-(dimethylamino)-8,11-dihydroxy-5-methyl-10,12-dioxo-5,6,6a,7,10,12-hexahydrotetracene-1,5,6,10a(5aH)-tetrayl tetraacetate

Conditions

Conditions	Yield
With dmap In dichloromethane at 0 - 25℃; for 1.5h;	72%

: 50-00-0
formaldehyd

: 79-57-2
Oxytetracycline

: 85721-33-1
ciprofloxacin

: 1-cyclopropyl-7-(4-{[(4-dimethylamino-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carbonyl)-amino]-methyl}-piperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Conditions

Conditions	Yield
In ethanol for 0.05h; Mannich reaction; microwave irradiation;	66%

...Expand

: 14099-01-5
rhenium(I) pentacarbonyl chloride

: 79-57-2
Oxytetracycline

: Re(oxytetracycline)(CO)3Cl

Conditions

Conditions	Yield
In toluene byproducts: CO; a mixt. in toluene was stirred for about 90 min at 70°C; ppt. was filtered, washed with toluene, pptn. from CH3CN-diethyl ether; elem. anal.;	60%

: 79-57-2
Oxytetracycline

: 66762-91-2
4-dedimethylamino-12a-deoxyterramycin

Conditions

Conditions	Yield
With zinc In acetic acid at 28℃; for 96h;	54%
With acetic acid; zinc

: 50-00-0
formaldehyd

: 79-57-2
Oxytetracycline

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: 7-(4-{[(4-dimethylamino-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carbonyl)-amino]-methyl}-piperazin-1-yl)-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Conditions

Conditions	Yield
In ethanol for 0.05h; Mannich reaction; microwave irradiation;	43%

...Expand

: 50-00-0
formaldehyd

: 79-57-2
Oxytetracycline

: 98079-51-7
lomefloxacin

: 7-(4-{[(4-dimethylamino-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carbonyl)-amino]-methyl}-3-methyl-piperazin-1-yl)-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Conditions

Conditions	Yield
In ethanol for 0.05h; Mannich reaction; microwave irradiation;	41%

...Expand

: 50-00-0
formaldehyd

: 79-57-2
Oxytetracycline

: 160738-57-8, 112811-59-3
gatifloxacin

: 1-cyclopropyl-7-(4-{[(4-dimethylamino-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carbonyl)-amino]-methyl}-3-methyl-piperazin-1-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Conditions

Conditions	Yield
In ethanol for 0.05h; Mannich reaction; microwave irradiation;	41%

...Expand

: 79-57-2
Oxytetracycline

A: α-apo-oxytetracycline

B: 4660-26-8
anhydro-oxytetracycline

C: α-apo-oxytetracycline

D: 569-33-5
terrinolide

Conditions

Conditions	Yield
With hydrogenchloride In water at 75℃; for 2h;	A 23.2% B n/a C 7.7% D 33.1%

...Expand

Downstream Products

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The Oxytetracycline, with the CAS registry number 79-57-2, is also known as 5-Hydroxytetracycline. Its EINECS number is 201-212-8. This chemical's molecular formula is C₂₂H₂₄N₂O₉ and molecular weight is 460.43. What's more, its systematic name is (4S,4aR,5S,5aR,6S,12aS) -4-(dimethylamino)-3,5,6,10,11,12a-hexahydroxy -6-methyl-1,12-dioxo-1,4,4a,5,5a,6,12,12a-octahydrotetracene -2-carboxamide. Its classification codes are: (1)Agricultural Chemical; (2)Anti-Bacterial Agents; (3)Anti-Infective Agents; (4)Drug / Therapeutic Agent; (5)Germicide, bactericide, disinfectant; (6)Human Data; (7)Mutation data; (8)Reproductive Effect. It is a tetracycline analog isolated from the actinomycete streptomyces rimosus and used in a wide variety of clinical conditions. It should be sealed and stored in a cool and ventilated place. Moreover, it should be protected from oxides, heat and fire. Oxytetracycline is a broad spectrum antibiotic that is active against a wide variety of bacteria. It is still used to treat infections caused by chlamydia. It is used to treat acne, due to its activity against the bacteria on the skin that cause acne. Moreover, it is also used to treat flare-ups of chronic bronchitis, due to its activity against the bacteria usually responsible, Haemophilus influenzae. It may also be used to treat other rarer infections, such as those caused by a group of micro-organisms called rickettsiae.

Physical properties of Oxytetracycline are: (1)ACD/LogP: 0.57; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): -0.71; (4)ACD/LogD (pH 7.4): -2.34; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 2.55; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 11; (10)#H bond donors: 8; (11)#Freely Rotating Bonds: 8; (12)Polar Surface Area: 113.07 Å²; (13)Index of Refraction: 1.762; (14)Molar Refractivity: 110.6 cm³; (15)Molar Volume: 268.1 cm³; (16)Polarizability: 43.84×10^-24cm³; (17)Surface Tension: 111.3 dyne/cm; (18)Density: 1.71 g/cm³; (19)Flash Point: 394 °C; (20)Enthalpy of Vaporization: 111.54 kJ/mol; (21)Boiling Point: 727.8 °C at 760 mmHg; (22)Vapour Pressure: 3.09E-22 mmHg at 25°C.

Preparation: it is derived by fermentation of Streptomyces rimosus (Streptomyces rimosus). You can get the product by drying the solid after adding calcium carbonate into the fermentation broth, followed by filtration.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to respiratory system and skin. It has a possible risk of harm to the unborn child. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. You should not breathe dust. When using it, you must avoid contact with eyes and need wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C4\C2=C(/O)c1c(cccc1O)[C@](O)(C)[C@H]2[C@H](O)[C@@H]3[C@@]4(O)C(=O)/C(C(=O)[C@H]3N(C)C)=C(\O)N
(2)Std. InChI: InChI=1S/C22H24N2O9/c1-21(32)7-5-4-6-8(25)9(7)15(26)10-12(21)17(28)13-14(24(2)3)16(27)11(20(23)31)19(30)22(13,33)18(10)29/h4-6,12-14,17,25-26,28,31-33H,23H2,1-3H3/b20-11-/t12-,13-,14+,17+,21-,22+/m1/s1
(3)Std. InChIKey: FYDOORKXBWEKQM-GUQPPTOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LDLo	intravenous	220mg/kg (220mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: FOOD INTAKE (ANIMAL) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Antibiotics and Chemotherapy Vol. 3, Pg. 1015, 1953.
guinea pig	LDLo	intraperitoneal	2250mg/kg (2250mg/kg)		Antibiotiki. Vol. 20, Pg. 793, 1975.
infant	TDLo	parenteral	136mg/kg (136mg/kg)	MUSCULOSKELETAL: CHANGES IN TEETH AND SUPPORTING STRUCTURES	Lancet. Vol. 1, Pg. 827, 1962.
man	TDLo	oral	114mg/kg/4D (114mg/kg)	BLOOD: HEMORRHAGE SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	JAMA, Journal of the American Medical Association. Vol. 231, Pg. 734, 1975.
mouse	LD50	intraperitoneal	5706mg/kg (5706mg/kg)		Antibiotiki. Vol. 20, Pg. 793, 1975.
mouse	LD50	intravenous	140mg/kg (140mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 1, 1955.
mouse	LD50	oral	2240mg/kg (2240mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 1, 1955.
mouse	LD50	subcutaneous	700mg/kg (700mg/kg)		"CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 3, Pg. 44, 1980.
rat	LD50	intravenous	260mg/kg (260mg/kg)		"Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 501, 1978.
rat	LD50	oral	4800mg/kg (4800mg/kg)		"Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 501, 1978.
women	TDLo	oral	24mg/kg/6D-I (24mg/kg)	BLOOD: THROMBOCYTOPENIA	American Journal of Hematology. Vol. 43, Pg. 333, 1993.

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Consensus Reports

Specification