Related Searches: Minoxidil

Minoxidil(CAS No. 38304-91-5)

Minoxidil C9H15N5O (cas 38304-91-5) Molecular Structure

38304-91-5 Structure

Identification and Related Records

【Name】
Minoxidil
【CAS Registry number】
38304-91-5
【Synonyms】
Mimosine
Minoxidil(USP 24)
Minoxidil USP/BP
Loniten (TN)
U-10,858
2,4-Diamino-6-piperidinopyrimidine 3-N-oxide
Prexidil
6-Amino-1,2-dihydro-1-hydroxy-2-imino-4-piperidinopyrimidine
Alopexil
U 10858
Regaine
Minossidile [Italian]
Prestwick_521
Minoximen
2,4-Pyrimidinediamine, 6-(1-piperidinyl)-, 3-oxide
Loniten
2,3-Dihydro-3-hydroxy-2-imino-6-(1-piperidinyl)-4-pyrimidinamine
Minoxidilum [INN-Latin]
Pyrimidine, 2,4-diamino-6-piperidino-, 3-oxide
Minoxidil (USP)
PDP
Tricoxidil
6-(1-Piperidinyl)-2,4-pyrimidinediamine 3-oxide
2,6-Diamino-4-piperidinopyrimidin-1-oxid
Rogaine
Alostil
3-hydroxy-2-imino-6-(1-piperidyl)pyrimidin-4-amine
6-Piperidino-2,4-diaminopyrimidine 3-oxide
2,4-Pyrimidinediamine,6-(1-piperidinyl)-,3- oxide
2,4-Diamino-6-piperidinopyrimidine 3-oxide
2,4-Diamino-6-piperidinilpirimidina-3-ossido [Italian]
Theroxidil
4-Pyrimidinamine, 2,3-dihydro-3-hydroxy-2-imino-6-(1-piperidinyl)-
【EINECS(EC#)】
253-874-2
【Molecular Formula】
C9H15N5O (Products with the same molecular formula)
【Molecular Weight】
209.25
【Inchi】
InChI=1/C9H15N5O/c10-7-6-8(12-9(11)14(7)15)13-4-2-1-3-5-13/h6H,1-5,10H2,(H2,11,12)
【InChIKey】
ZFMITUMMTDLWHR-UHFFFAOYSA-N
【Canonical SMILES】
C1CCN(CC1)C2=NC(=N)N(C(=C2)N)O
【MOL File】
38304-91-5.mol

Chemical and Physical Properties

【Appearance】
White crystalline powder
【Density】
1.52 g/cm3
【Melting Point】
272-274 °C (dec.)(lit.)
【Boiling Point】
351.7 °C at 760 mmHg
【Refractive Index】
1.724
【Flash Point】
166.5 °C
【Water】
Soluble in ethanol (29mg/ml), DMSO (6.5mg/ml), and water (2.2mg/ml)
【Solubilities】
Soluble in ethanol (29mg/ml), DMSO (6.5mg/ml), and water (2.2mg/ml)
【Color/Form】
Crystals from methanol-acetonitrile
White to off-white, crystalline powder
【Stability】
Stable at normal temperatures and pressures.
【Storage temp】
Keep in a cool, dry location. Keep containers closed when not in use. Protect from light.
【Spectral properties】
Maximum absorption (ethanol): 230, 261, 285 nm (E= 35210, 11210, 11790); (0.01 N sulfuric acid: 232, 280 nm (E= 26350, 23850); (0.01 N potassium hydroxide): 231, 261.5, 285 nm (E= 36100, 11400, 12040).
【Computed Properties】
Molecular Weight:209.2483 [g/mol]
Molecular Formula:C9H15N5O
XLogP3:1.2
H-Bond Donor:3
H-Bond Acceptor:3
Rotatable Bond Count:1
Tautomer Count:4
Exact Mass:209.12766
MonoIsotopic Mass:209.12766
Topological Polar Surface Area:88.9
Heavy Atom Count:15
Formal Charge:0
Complexity:329
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Donor Count:2
Feature 3D Cation Count:2
Feature 3D Ring Count:2
Effective Rotor Count:2.2
Conformer Sampling RMSD:0.6
CID Conformer Count:4

Safety and Handling

【Hazard Codes】
Xn: Harmful;
【Risk Statements】
R22;R36/37/38
【Safety Statements 】
S26;S36;S45;S36/37/39;S22
【Safety】

Hazard Codes:?HarmfulXn,VeryT+
Risk Statements: 22-36/37/38-26/27/28?
R22:Harmful if swallowed.?
R26/27/28:Very toxic by inhalation, in contact with skin and if swallowed.?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-45-36/37/39-22?
S22:Do not breathe dust.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36:Wear suitable protective clothing.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.?
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

【Formulations/Preparations】
Tablets, 2.5 and 10 mg (Loniten). Topical soluton, 2% (Rogaine)
Oral tablets: 2.5 and 10 mg (scored)-Loniten (also Australia, United Kingdom).
Topical Solution, 2% Hair Regrowth /SRP: retail pharmaceutical distributor/; Rogaine Hair Regrowth Treatment for Men (with alcohol 60% and propylene glycol), Pharmacia; Rogaine Hair Regrowth Treatment for Women (with alcohol 60% and propylene glycol), Pharmacia. 5% Rogaine Extra Strength for Men (with alcohol 30% and propylene glycol), Pharmacia.
Oral Tablets, 2.5 mg, Loniten (scored), Pharmacia; 10 mg, Loniten (scored), Pharmacia.
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl minoxidil, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
【Specification】

?Minoxidil?, its cas register number is 38304-91-5. It also can be called 6-(1-Piperidinyl)-2,4-pyrimidinediamine-3-oxide ; Loniten ; Regain ; Rogaine ; and 2,4-Diamino-6-piperidino-pyrimidine-3-oxide .?In 2007 a new foam-based formulation of 5% minoxidil was shown to be as effective as the liquid-based treatment for male pattern baldness.

【Octanol/Water Partition Coefficient】
log Kow = 1.24
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Preparation: NL 6615385; W. C. Anthony et al, US 3382247 (1967, 1968 both to Upjohn); ... W. C. Anthony, US 3644364 (1972 to Upjohn).
【Usage】

Used as an antihypertensive and antialopecia agent. Minoxidil activates ATP-activated K+ channels

Biomedical Effects and Toxicity

【Biological Activity】
Antihypertensive. Antialopecia agent. K + channel (K ATP ) activator.
【Pharmacological Action】
- Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.
- Drugs used to cause dilation of the blood vessels.
【Therapeutic Uses】
Antihypertensive Agents; Vasodilator Agents
Minoxidil is indicated for treatment of hypertension. Because of its serious side effects, minoxidil is not considered to be a primary agent in the treatment of essential hypertension. It is recommended for use only in patients with symptomatic or organ-damaging hypertension not responsive to other treatment. /Included in US product labeling/
Minoxidil is used topically to stimulate regrowth of hair in balding areas of individuals with androgenetic alopecia (male pattern alopecia, hereditary alopecia, common male baldness). The drug is effective in promoting hair regrowth on the vertex (crown) of the scalp but appears to have little or no effect on temporal recession; the efficacy of topical minoxidil therapy for frontal alopecia has not been evaluated objectively to date. There is evidence to suggest that individuals most likely to respond to topical minoxidil therapy are those younger than 40 years of age, those in whom treatment is initiated relatively early (less than 10 years' duration of hair loss), those with a small diameter of baldness (less than 10 cm), and those who have a large number of terminal or indeterminate (intermediate) hairs before initiation of treatment. At least 4 mo of continuous therapy with minoxidil topical solution usually is required for evidence of response; however, treatment for up to a year may be warranted before deciding that the alopecia is unresponsive. While the ultimate benefit of topical minoxidil therapy depends on the subjective perceptions of the treated individual, cosmetically acceptable hair regrowth as determined by study investigators has been reported in approximately one third of individuals after 6-12 mo of twice daily therapy in most clinical studies, and complete coverage of the balding areas of the scalp occurs rarely. Current evidence suggests that such therapy must be continued indefinitely for maintenance of hair growth.
Topically applied minoxidil has been used as a 1, 3, or 5% solution, ointment, or cream to promote hair regrowth in males and females with alopecia areata, including those with the most severe forms, alopecia totalis (complete loss of scalp hair) or alopecia universalis (complete loss of body hair). Overnight petrolatum occlusion of the treated area, which has been reported to enhance efficacy, has been used in some studies. A cosmetically acceptable response to topical minoxidil therapy appears most likely to occur in patients with patchy alopecia areata; patients with total loss of scalp or body hair at baseline (eg; those with alopecia totalis or universalis) usually have the poorest and most delayed response. Efficacy of any therapy in patients with alopecia areata is difficult to evaluate because of the spontaneous hair regrowth and hair loss characteristic of the disease. As in androgenetic alopecia, some patients with alopecia areata receiving treatment with the vehicle alone in controlled studies have had regrowth of terminal hair, and hair loss has resumed in other patients during continued topical minoxidil therapy.
Topical minoxidil therapy has been used as an adjunct to hair transplantation. Limited evidence suggests that the drug may promote better evolution of hair grafts by reducing postoperative shedding of hair and hastening the onset of postshedding hair regrowth.
...The charts of 60 women with a mean age of 58 years who underwent primary cervicofacial rhytidectomy were studied. Either a standard SMAS/flap technique or pliation was done in all cases. Each patient received either 2% or 5% topical minoxidil for 2 weeks before surgery and for 4 weeks after surgery, with a 5-day break period beginning on the day of surgery. Patients were monitored for complications immediately postoperatively and in 3-6 months of follow-up. Almost 80% of the patients underwent SMAS/flap procedures. Transient temporal alopecia was noted in only one patient, 6 weeks after discontinuing minoxidil. This resolved within 4 weeks of its reintroduction. The only other complications noted included minor hematomas (3.3%), skin slough/infection (1.7%), minor transient and localized edema (8.3%), minor ecchymosis (1.7%), a unilateral neuropraxia of the buccal nerve lasting 3 months (1.7%), and a minor temporary unilateral skin depression (1.7%). Side effects of minoxidil were not observed. ... [Eremia S et al; Dermatol Surg 28 (1): 66-74 (2002)]
【Biomedical Effects and Toxicity】
Minoxidil is almost completely absorbed (95%) from the GI tract. Peak plasma levels are reached in 1 hr. Protein binding does not occur. Minoxidil is widely distributed in the tissues, with an apparent volume of distribution of about 2.8-3.3 l/kg. Placental passage and distribution into breast milk have not been established. The elimination half-life of minoxidil is2.77-4.2 hr. About 90% of an oral dose of minoxidil is metabolized in the liver. The drug and its metabolites are largely excreted in the urine. Renal clearance is 73.9 ml/min.
Percutaneous absorption of minoxidil appears to be minimal following topical application of minoxidil solution to intact scalp. However, systemic absorption of topically applied minoxidil is variable and depends on several factors, including the vehicle used in the formulation, the area of application, condition of the skin (eg; being increased with local abrasion or inflammation), and interindividual variation in the extent of percutaneous absorption. Percutaneous absorption of the drug does not appear to be altered by use of a hot-air hair dryer. Although limited in vitro evidence suggests comparable release of minoxidil from solutions with different proportions of propylene glycol, alcohol, and water, release of the drug from a cream base differs substantially from that from solution formulations, and water-in-oil creams appear to differ markedly from oil-in-water creams or ointments in terms of the rate and concentration dependency of drug permeation through human skin. Absorption of minoxidil from extemporaneously prepared solutions, ointments, creams, or other such topical formulations may not be comparable to that from the commercially available topical minoxidil solution.
Percutaneous absorption of minoxidil following topical application of 2% hydroalcoholic, propylene glycol-containing solutions of the drug generally has been reported to average 0.3-4.5% of the applied dose. In a preliminary study in healthy balding men, the systemic bioavailability of minoxidil 2 or 3% topical solution (20 or 30 mg doses, respectively) at steady state relative to that of a 2.5 mg oral tablet averaged 1.4 or 1.2%, respectively. Based on urinary excretion of radiolabeled drug administered to healthy men in another study, percutaneous absorption of minoxidil after application of 1 or 5% minoxidil solutions to the scalp generally averaged 1.6-3.9% of the applied dose, based on urinary recovery of radiolabeled drug. In studies in animals, 5-36% of topically applied doses was absorbed systemically. Serum concentrations achieved after topical application of minoxidil solutions are variable, and clinical studies of topical minoxidil therapy have found no correlation between serum minoxidil concentrations and hair growth. In controlled studies in individuals with androgenetic alopecia or alopecia areata, serum concentrations of minoxidil after topical application of 1, 2, 3, or 5% solution formulations (with or without nightly petrolatum occlusion) generally averaged 2 ng/ml or less. However, about 1% of individuals receiving a 2% topical solution achieved peak serum concentrations of 5 ng/ml or greater, and a few patients achieved concentrations approaching 30 ng/ml. In part, increased percutaneous absorption of the drug in some individuals may have resulted from alterations in the stratum corneum (eg; secondary to irritation and inflammation from shaving of the scalp). In addition, some individuals may have a propensity for enhanced percutaneous absorption of the drug. Data from healthy balding men indicate that peak serum concentrations of unchanged minoxidil after oral doses of 5 mg daily generally are 20-30 times higher than mean serum concentrations achieved after twice daily topical application of approximately 20 mg (1 ml) of minoxidil as a 2% solution.
The distribution of topically applied minoxidil has not been fully determined. Limited evidence suggests that intact stratum corneum serves as a barrier that inhibits substantial diffusion of topically applied minoxidil into systemic circulation, but additional study is needed. Skin biopsy specimens obtained after topical application of a radiolabeled minoxidil 1 or 5% solution to the scalp of healthy balding men indicate an average retention in the skin of 2.6% or less of the applied dose after 24 hr, with twice as much radioactivity in the dermis as in the epidermis. The remainder of the dose remained on the skin or presumably was lost to the environment.
The distribution of minoxidil into milk following topical application of the drug is not known, but the drug has been shown to distribute into milk following oral administration in lactating women.
The metabolic fate and elimination characteristics of topically applied minoxidil have not been fully determined. A study in healthy men receiving radiolabeled drug indicates that following topical application, systemically absorbed minoxidil is excreted principally in urine; no fecal radioactivity was detected in this study. Following cessation of topical minoxidil dosing, approximately 95% of systemically absorbed drug is eliminated within 4 days. An appreciable portion of a topically applied dose appears to be removed from the surface of the scalp via inadvertent contact with hands or clothing, volatilization, displacement by air currents, or other nonsystemic means.
Plasma concentrations of minoxidil do not correlate with extent or duration of action, probably because the drug exerts a persistent effect at receptor sites. After a single 2.5 to 25 mg oral dose of minoxidil, the hypotensive effect begins in 30 min, is maximal in 2-8 hr, and persists for about 2-5 days.
The drug and its metabolites are excreted principally in urine by glomerular filtration; with chronic therapy in patients with renal impairment, minoxidil's glucuronide metabolites accumulate in plasma but the unchanged drug does not. Minoxidil and its metabolites can be removed by hemodialysis or peritoneal dialysis.

Supplier Location

Top Suppliers

Diamond member Nanjing Bangnuo Biotechnology Co., Ltd.
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-25-52178272
Diamond member Hubei XinRunde Chemical Co., Ltd
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-188-74586545
Diamond member chengdu yancey import& export trade co.,ltd
Country:ChinaChina
Business Type:Trading Company
Telephone:86-153-73023168
Diamond member Shanghai Do Chemical Co.,Ltd
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-21-33758180
Diamond member Hangzhou Dayangchem Co., Ltd.
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-571-88938639
Diamond member Wuhan Fortuna Chemical Co., Ltd.
Country:ChinaChina
Business Type:Manufacturer
Telephone:0086-27-59207850
Diamond member MOSINTER GROUP LIMITED
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-574-89212210
Diamond member AOPHARM
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-311-66600578
Diamond member Yichang yongnuopharm co.,ltd
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-717-4128488
Diamond member Nanjing Chemlin Chemical Co., Ltd.
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-25-83697070

Quick Search

Cas    Name

Related products

minoxidil sulfate

Minoxidil, Sulfate; minoxidilsulfateester; 6-(1-PIPERIDINYL)-2,4-PYRIMIDINEDIAMINE-3-OXIDE SULFATE; MINOXIDIL SULPHATE; U-58838; MINOXIDIL SUFATE ETHY...

MINOXIDIL GLUCURONIDE

MINOXIDIL GLUCURONIDE;6-(1-PIPERIDINYL)-2,4-PYRIMIDINEDIAMINE-3-OXIDE GLUCURONIDE

MINOXIDIL-D10

MINOXIDIL-D10;MINOXIDIL-D10 (PIPERIDINE-D10);6-(1-PIPERIDINYL)-2,4-PYRIMIDINEDIAMINE-3-OXIDE-D10;2,4-DiaMino-6-(piperidino-d10) pyriMidine 3-N-Oxide;6...

Minoxidil IMpurity D

Minoxidil IMpurity D;2,6-DiaMino-4-pyriMidinyl p-Toluenesulfonate 3-Oxide