Minocycline

Base Information

• Chemical Name: Minocycline
• CAS No.: 10118-90-8
• Molecular Formula: C23H27N3O7
• Molecular Weight: 457.483
• Mol file: 10118-90-8.mol

Synonyms:2-Naphthacenecarboxamide,4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-(8CI);2-Naphthacenecarboxamide,4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-,[4S-(4a,4aa,5aa,12aa)]-;CL 59806;Dynacin;Minocyclin;Minocyn;Tri-minocycline;2-Naphthacenecarboxamide,4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-,(4S,4aS,5aR,12aS)-;

Chemical Property of Minocycline

Chemical Property:

• Appearance/Colour: Bright yellow-orange amorphous solid.
• Refractive Index: 1.717
• Boiling Point: 659.401 °C at 760 mmHg
• PKA: pKa 2.8 (Uncertain);5.0 (Uncertain);7.8 (Uncertain);9.5 (Uncertain)
• Flash Point: 352.593 °C
• PSA: 164.63000
• Density: 1.553 g/cm³
• LogP: 0.88690
• Water Solubility.: 52g/L(25 oC)

Purity/Quality:

99%min ^*data from raw suppliers

Minocycline 99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Minocycline belongs to the class of medications called tetracycline antibiotics, who has a broader spectrum than the other members of the group. Identified as a long-acting type, it is used to treat infections induced by certain kinds of bacteria. Minocycline is commonly used in the treatment of skin infections, such as inflammatory lesions of non-nodular moderate-to-severe acne vulgaris. It is also used for other skin infections, such as MRSA and Lyme disease. Besides, minocycline is effective to treat urinary tract infections, gallbladder infections, and respiratory tract infections like bronchitis, pneumonia, sinusitis and it is also used for treating Rocky Mountain spotted fever, typhus and other infections caused by the typhus group of bacteria and tick fevers caused by rickettsiae, etc. Patented in 1961, minocycline was put into commercial use in 1971. It is not a naturally occurring antibiotic, but was synthesized semi-synthetically from natural tetracycline antibiotics by Lederle Laboratories in 1966. An important antibiotic produced by semisynthesis from demeclocycline is minocycline. It is much more lipophilic than its precursors, gives excellent blood levels following oral administration (90–100% available),and can be given once a day. Its absorption is lowered by approximately 20% when taken with food or milk. It is less dependent on active uptake mechanisms and has a somewhat broader antimicrobial spectrum. It also, apparently, is less painful on IM or IV injection, but it has vestibular toxicities (e.g., vertigo, ataxia, and nausea) not generally shared by other tetracyclines.
• Uses: Minocycline is used for the same indications as other antibiotics of the tetracycline series. In a few cases, it is tolerated worse than other tetracyclines, and in particular, it has an effect on the vestibular apparatus. In addition, as seen already from the synthesis scheme, it is much more expensive than other tetracyclines, which are synthesized in a purely microbiological manner. Synonyms of this drug are clinocin, minocyn, vectrin, and others. Minocycline is a semi-synthetic tetracycline prepared by sequential hydrogenolysis, nitration and reductive methylation. Minocycline, together with doxycycline, is regarded as a ‘third generation’ tetracycline largely replacing the natural products and pro-drugs produced in the early 1950s for mainstream antibiotic applications. Like all tetracyclines, minocycline shows broad spectrum antibacterial and antiprotozoan activity and acts by binding to the 30S and 50S ribosomal sub-units, blocking protein synthesis. Minocycline has been extensively cited in the literature with over 5,000 references.
• Indications: The tetracycline antibiotic minocycline (Minocin) is modestly effective in the treatment of rheumatoid arthritis and is generally well tolerated. Radiographic evidence of its efficacy as a DMARD is lacking, although clinical symptoms do abate. It can be useful in the treatment of early, mild disease.
• Therapeutic Function: Antibiotic
• Clinical Use: There appear to be few situations in which it has a unique therapeutic advantage over other tetracyclines. Its use has been tempered by the high incidence of vestibular side effects. Although used in the long-term management of acne, the potential for skin pigmentation must be considered. Because of its high tissue concentrations, it may occasionally provide a useful alternative to other agents for the treatment of chronic prostatitis. It has a role in the treatment of sexually transmitted chlamydial infections.
• Drug interactions: Potentially hazardous interactions with other drugs Anticoagulants: possibly enhanced anticoagulant effect of coumarins and phenindione. Oestrogens: possibly reduced contraceptive effect of oestrogens (risk probably small). Retinoids: possibly increased risk of benign intracranial hypertension - avoid.

Technology Process of Minocycline

There total 17 articles about Minocycline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

3,10,12,12a- tetraacetylminocycline → MINOCYCLINE (10118-90-8)

Guidance literature:

With methanol; lithium hydroxide; at 0 - 20 ℃; for 2h; Reagent/catalyst;

Reference yield: 85.0%

[4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide (149934-19-0) → MINOCYCLINE (10118-90-8)

Guidance literature:

With nitrous acid isobutyl ester; In N,N-dimethyl-formamide; at 70 ℃; for 0.75h;

Reference yield: 68.0%

(dimethylamino)trimethyltin (993-50-0) + [4S-(4α,12aα)]-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-7-iodo-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydronaphthacene-2-carboxamide (113164-67-3) → MINOCYCLINE (10118-90-8)

Guidance literature:

dichlorobis(tri-O-tolylphosphine)palladium; In toluene; for 8h; Heating;

DOI:10.1021/jo0256585

upstream raw materials:

azetidine

(dimethylamino)trimethyltin

[4S-(4α,12aα)]-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-7-iodo-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydronaphthacene-2-carboxamide

morpholine

Downstream raw materials:

(4S,4aS,5aR,12S)-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-nitro-1,11-dioxanaphthacene-2-carboxamide

[4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide

(4aS,5aR,12aS)-9-Benzoyl-7-dimethylamino-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide

9-(4-methylphenyl)thiocarboxylacyl-4-dedimethylamino-minocycline

Refernces

• 1、 -. "Synthesis method of minocycline hydrochloride". Paragraph 0022; 0048-0051. . Retrieved 2021/03/31.
• 2、 -. "Preparation method of minocycline hydrochloride". Paragraph 0056; 0064; 0072; 0079; 0094; 0101. . Retrieved 2017/08/30.