914-00-1 Usage
Uses
Used in Human Medicine:
Methacycline is used as an antibiotic for the same indications as other antibiotics of the tetracycline series. It is particularly useful in cases where it is better tolerated than other tetracyclines.
Used in Veterinary Medicine:
Methacycline is a potential veterinary drug, used as a broad-spectrum antibacterial and antiprotozoal agent for the treatment of various infections in animals.
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).
Check Digit Verification of cas no
The CAS Registry Mumber 914-00-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,1 and 4 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 914-00:
(5*9)+(4*1)+(3*4)+(2*0)+(1*0)=61
61 % 10 = 1
So 914-00-1 is a valid CAS Registry Number.
InChI:InChI=1/C22H22N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-6,10,14-15,17,25-27,31-32H,1,23H2,2-3H3/b21-13+/t10-,14-,15+,17+,22+/m1/s1
914-00-1Relevant academic research and scientific papers
Compositions and methods for treating hemorrhagic virus infections and other disorders
-
, (2008/06/13)
Cytokine-receptor and cytokine antagonist-enriched blood-dervided compositions and methods of preparing and using the compositions are provided. Also provided are compositions and methods for the treatment or prevention of disorders, especially acute inflammatory disorders involving pathological responses of the immune system, such as viral hemorrhagic diseases, sepsis, rheumatoid arthritis and other autoimmune disorders, acute cardiovascular events, flare-ups and acute phases of multiple sclerosis, wasting disorders and other disorders involving deleterious expression of cytokines and other factors, including tumor necrosis factor (TNF) and interleukin-1 (IL-1) are provided.
Manufacture of 6-methylenetetracyclines
-
, (2008/06/13)
Methacycline (6-methylene-5-oxytetracycline) is prepared by halogenating oxytetracycline (5-hydroxytetracycline) to produce the 11a-halo-6,12-hemiketal, under conditions which form and maintain the product in the enolic form, reacting the hemiketal base with acid to produce the hemiketal acid salt, dehydrating the acid salt to form 11a-halo-6-methylene-5-oxytetracycline, and reducing the compound to the salt of 6-methylene-5-oxytetracycline. An improved method for producing the 6-methylenetetracycline base from the product salt is also disclosed. The process is applicable to the synthesis of 6-methylenetetracycline per se or other 6-methylenetetracyclines, as well as methacycline.
