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METHACYCLINE

Product Name
METHACYCLINE
CAS No.
914-00-1
Chemical Name
METHACYCLINE
Synonyms
Metacyclin;rondomycin;gs-2876;bialatan;METHACYCLINE;12aalpha))-ph;methacyclinebase;tri-methacycline;methacyclineamphoteric;METHACYCLINE USP/EP/BP
CBNumber
CB0105251
Molecular Formula
C22H22N2O8
Formula Weight
442.42
MOL File
914-00-1.mol
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METHACYCLINE Property

Melting point:
205 °C (decomp)
Boiling point:
553.06°C (rough estimate)
Density 
1.4033 (rough estimate)
refractive index 
1.6500 (estimate)
storage temp. 
Refrigerator
solubility 
Methanol (Slightly), Water (Slightly)
form 
Solid
pka
pKa 3.5 (Uncertain);7.6 (Uncertain);9.5(EtOH/H2O t=20.0) (Uncertain)
color 
Yellow to Brown
Water Solubility 
7.548g/L(21 ºC)
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Safety

Hazardous Substances Data
914-00-1(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

TRC
Product number
M258788
Product name
Methacycline
Packaging
100mg
Price
$1115
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0003319
Product name
METHACYCLINE
Purity
95.00%
Packaging
100MG
Price
$428
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0003319
Product name
METHACYCLINE
Purity
95.00%
Packaging
1G
Price
$680
Updated
2021/12/16
AvaChem
Product number
1999B
Product name
Metacycline
Packaging
100mg
Price
$59
Updated
2021/12/16
AvaChem
Product number
1999B
Product name
Metacycline
Packaging
1g
Price
$290
Updated
2021/12/16
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METHACYCLINE Chemical Properties,Usage,Production

Description

Methacycline was synthesized by Pfizer Research Laboratories in 1961 starting with oxytetracycline. It shows two to fivefold greater in vitro antibacterial activity and in vivo protective activity than tetracycline. Methacycline has been given orally to treat infections by Rickettsia, Chlamydiae, Staphyloccus, Streptococcus, Neisseria, Klebsiella, Proteus, Escherichia coli, and Haemophilus influenzae.

Originator

Rondomycin ,Pfizer ,UK ,1963

Uses

Methacycline is used for the same indications as other antibiotics of the tetracycline series. In some cases it is tolerated better than tetracyclines. Synonyms of this drug are rondomycin, methamycin, adramycin, and others.

Uses

Methacycline is a tetracycline with broad range antibacterial and antiprotozoal properties. Potential veterinary drug.

Uses

Methacycline is a semi-synthetic tetracycline prepared by dehydration of the 6-hydroxy group of oxytetracycline to yield an exocyclic 6-methylene. Like all tetracyclines, methacycline shows broad spectrum antibacterial and antiprotozoan activity and acts by binding to the 30S and 50S ribosomal subunits, blocking protein synthesis. Methacycline has been extensively cited in the literature with over 400 references.

Definition

ChEBI: A tetracycline that is the 6-methylene analogue of oxytetracycline, obtained by formal dehydration at position 6.

Manufacturing Process

To a stirred solution of 4.6 g (0.01 mol) of anhydrous oxytetracycline in 40 ml of dry tetrahydrofuran is added 3.5 g (0.021 mol) of pyridine-sulfur trioxide complex. After 16 hours of stirring at room temperature, the resulting suspension is filtered, and the solid is slurried with 25 ml of 2% hydrochloric acid for 10 minutes, filtered and thoroughly washed with methanol followed by ether. The pale yellow crystalline 5-oxytetracycline-6,12-hemiketal-12-sulfuric acid ester melts at 210°C.
500 mg 5-oxytetracycline-6,12-hemiketal-12-sulfuric acid ester, prepared as described, is added to 4 ml dry liquid hydrogen fluoride, and the mixture is stirred for 1.5 hours at ice bath temperature. The hydrogen fluoride is then evaporated in a stream of nitrogen and the resulting gummy solids are triturated with about 15 ml ether and filtered. The resulting solid hydrofluoride salt is further purified by suspending in water, adjusting the pH to about 4, and extracting the 6-methylene-5-oxytetracycline free base from the aqueous phase with ethyl acetate. The extract is separated and evaporated to dryness under reduced pressure. The resulting residue is triturated with ether and filtered, and the solid is recrystallized from methanol-acetone-etherconcentrated hydrochloric acid to obtain the product as a purified hydrochloride, according to US Patent 3,026,354.

brand name

Rondomycin (Medpointe).

Therapeutic Function

Antibiotic

Pharmaceutical Applications

6-Methylene-5-hydroxy-tetracycline. A semisynthetic derivative supplied as the hydrochloride for oral administration.
Mean peak plasma concentrations of 2–6 mg/L are found about 4 h after a 300 mg oral dose. Both food and milk reduce uptake by half. Protein binding is 80–90%. The plasma elimination half-life varies between 7 and 15 h and increases to 44 h in severe renal impairment. It is widely distributed, producing lung concentrations similar to, or greater than, the simultaneous plasma concentration. About one-third is excreted in the urine.
Gastrointestinal intolerance is reported to be less frequent than with other tetracyclines, largely because of the lower dosages used. There are no unique adverse drug reactions, although skin and conjunctival pigmentation have been reported.

Synthesis

Methacycline, 4-dimethylamino-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10, 12,12a-pentahydroxy-6-methylen-1,11-dioxo-2-naphthacencarboxamide (32.3.6), is synthesized from oxytetracycline (32.3.2), which is reacted with a sulfur trioxide—pyridine complex, resulting in an oxidation reaction. Simultaneous sulfonation gives a naphthacen–sulfotetrahydrofuran derivative intermediate (32.3.5), which when reacted with hydrofluoric acid forms methacycline (32.3.6).

METHACYCLINE Preparation Products And Raw materials

Raw materials

Preparation Products

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METHACYCLINE Suppliers

Hunan Hui Bai Shi Biotechnology Co., Ltd.
Tel
0731-85526065 13308475853
Email
ivy@hnhbsj.com
Country
China
ProdList
4552
Advantage
62
Hangzhou Yuhao Chemical Technology Co., Ltd
Tel
0571-82693216
Fax
+86-571-82880190
Email
info@yuhaochemical.com
Country
China
ProdList
9387
Advantage
52
Beijing HuaMeiHuLiBiological Chemical
Tel
010-56205725
Fax
010-65763397
Email
waley188@sohu.com
Country
China
ProdList
12335
Advantage
58
Shanghai Aladdin Bio-Chem Technology Co.,LTD
Tel
400-400-6206333 18521732826
Fax
021-50323701
Email
market@aladdin-e.com
Country
China
ProdList
25003
Advantage
65
ChemStrong Scientific Co.,Ltd
Tel
0755-0755-66853366 13670046396
Fax
0755-28363542
Email
sales@chem-strong.com
Country
China
ProdList
18043
Advantage
56
Alta Scientific Co., Ltd.
Tel
022-6537-8550 15522853686
Fax
022-2532-9655
Email
sales@altasci.com.cn
Country
China
ProdList
4511
Advantage
55
Raw material medicin reagent co.,Ltd
Tel
Email
sales@njromanme.com
Country
China
ProdList
4529
Advantage
58
Lynnchem
Tel
86-(0)29-85992781 17792393971
Email
info@lynnchem.com
Country
China
ProdList
4587
Advantage
58
Novachemistry
Tel
44-20819178-90 02081917890
Fax
(0)2080432064
Email
info@novachemistry.com
Country
United Kingdom
ProdList
4381
Advantage
58
Shenzhen SUNGENING Bio-Medical Co., Ltd.
Tel
0755-28967200 13631290199
Fax
0755-28967200
Email
wxf@sungening.com
Country
China
ProdList
9577
Advantage
60
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View Lastest Price from METHACYCLINE manufacturers

Apeloa production Co.,Limited
Product
methacycline 914-00-1
Price
US $1.00/g
Min. Order
1g
Purity
0.98
Supply Ability
1000
Release date
2024-07-18
Shaanxi Dideu Medichem Co. Ltd
Product
Metacyclin 914-00-1
Price
US $0.00-0.00/Kg
Min. Order
1KG
Purity
99.0%+
Supply Ability
300 MT
Release date
2020-05-23

914-00-1, METHACYCLINERelated Search:


  • methacyclinebase
  • rondomycin
  • tri-methacycline
  • (4S,4aR,5S,5aR,12aS)-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-2-naphthacenecarboxamide
  • 6-Methyleneoxytetracycline, Metacycline, RondoMycin
  • METHACYCLINE
  • ,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-
  • 10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-,(4s-(4alpha,4aalpha,5alpha,5aal
  • 12aalpha))-ph
  • 6-demethyl-6-deoxy-5-hydroxy-6-methylenetetracycline
  • 6-deoxy-6-demethyl-6-methylene-5-oxytetracycline
  • 2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-,(4S,4aR,5S,5aR,12aS)-
  • Doxycycline Impurity 2(Doxycycline EP Impurity B)
  • Metacyclin
  • 6-methylene-5-hydroxytetracycline
  • 6-methylene-5-oxytetracycline
  • 6-methylene-oxytetracyclin
  • 6-methyleneoxytetracycline
  • bialatan
  • gs-2876
  • methacyclineamphoteric
  • Doxycycline EP Impurity B/Metacycline
  • METHACYCLINE USP/EP/BP
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  • tetrabutylazanium,2,4,6-trinitrophenolate
  • Doxycycline impurity B
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  • 914-00-1