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药品详细

Vitamin A(维生素A)

化学结构式图
中文名
维生素A
英文名
Vitamin A
分子式
C20H30O
化学名
3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol
分子量
Average: 286.4516
Monoisotopic: 286.229665582
CAS号
68-26-8
ATC分类
A11C 未知;D10A Anti-Acne Preparations for Topical Use;S01X 其他眼科用药;R01A 未知
药物类型
small molecule
阶段
approved, nutraceutical
商品名
同义名
基本介绍

Retinol and derivatives of retinol that play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response. Dietary vitamin A is derived from a variety of carotenoids found in plants. It is enriched in the liver, egg yolks, and the fat component of dairy products. [PubChem]

生产厂家
  • Arcum pharmaceutical corp
  • Astrazeneca lp
  • Banner pharmacaps inc
  • Bayer pharmaceuticals corp
  • Bel mar laboratories inc
  • Bristol myers squibb co
  • Chase chemical co lp
  • Del ray laboratories inc
  • Eli lilly and co
  • Elkins sinn div ah robins co inc
  • Everylife
  • Hospira inc
  • Impax laboratories inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mk laboratories inc
  • Sterling winthrop inc
  • Teva pharmaceuticals usa inc
  • West ward pharmaceutical corp
  • Wharton laboratories inc div us ethicals
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. Roncone DP: Xerophthalmia secondary to alcohol-induced malnutrition. Optometry. 2006 Mar;77(3):124-33. Pubmed
剂型
规格
化合物类型
Type small molecule
Classes
  • Retinoids
Substructures
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Alcohols and Polyols
  • Monoterpenes
  • Isoprenes
  • Retinoids
  • Cyclohexenes and Derivatives
适应症
药理
Indication For the treatment of vitamin A deficiency.
Pharmacodynamics Vitamin A is effective for the treatment of Vitamin A deficiency. Vitamin A refers to a group of fat-soluble substances that are structurally related to and possess the biological activity of the parent substance of the group called all-trans retinol or retinol. Vitamin A plays vital roles in vision, epithelial differentiation, growth, reproduction, pattern formation during embryogenesis, bone development, hematopoiesis and brain development. It is also important for the maintenance of the proper functioning of the immune system.
Mechanism of action Vision:Vitamin A (all-trans retinol) is converted in the retina to the 11-cis-isomer of retinaldehyde or 11-cis-retinal. 11-cis-retinal functions in the retina in the transduction of light into the neural signals necessary for vision. 11-cis-retinal, while attached to opsin in rhodopsin is isomerized to all-trans-retinal by light. This is the event that triggers the nerve impulse to the brain which allows for the perception of light. All-trans-retinal is then released from opsin and reduced to all-trans-retinol. All-trans-retinol is isomerized to 11-cis-retinol in the dark, and then oxidized to 11-cis-retinal. 11-cis-retinal recombines with opsin to re-form rhodopsin. Night blindness or defective vision at low illumination results from a failure to re-synthesize 11-cis retinal rapidly.
Epithelial differentiation: The role of Vitamin A in epithelial differentiation, as well as in other physiological processes, involves the binding of Vitamin A to two families of nuclear retinoid receptors (retinoic acid receptors, RARs; and retinoid-X receptors, RXRs). These receptors function as ligand-activated transcription factors that modulate gene transcription. When there is not enough Vitamin A to bind these receptors, natural cell differentiation and growth are interrupted.
Absorption Readily absorbed from the normal gastrointestinal tract
Volume of distribution Not Available
Protein binding <5% of circulating vitamin A is bound to lipoproteins in blood in normal condition, but may be up to 65% when hepatic stores are saturated because of excessive intake. When released from liver, vitamin A is bound to retinol-binding protein (RBP). Most vitamin A circulates in the form of retinol bound to RBP.
Metabolism
Hepatic. Retinol is conjugated with glucuronic acid; the B-glucuronide undergoes enterohepatic circulation and oxidation to retinol and retinoic acid. Retinoic acid undergoes decarboxylation and conjugation with glucuronic acid.
Route of elimination Not Available
Half life 1.9 hours
Clearance Not Available
Toxicity Acute toxicity (single ingestion of 7 500 RE or 25 000 IU per kg or more): Signs and symptoms may be delayed for 8 to 24 hours and include: increased intracranial pressure, headache, irritability, drowsiness, dizziness, lethargy, vomiting, diarrhea, bulging of fontanels in infants, diplopia, papilledema. Peeling of skin around mouth may be observed from 1 to several days after ingestion and may spread to the rest of the body. Chronic, excessive ingestion (1 200 RE or 4 000 IU/kg daily for 6 to 15 months) may produce symptoms of pseudotumor cerebri, anorexia, weakness, arthralgias, bone pain, bone demineralization, dry skin, cracked lips, brittle nails, hair loss, splenomegaly, hepatomegaly, hypoplastic anemia, leukopenia, optic neuropathy, and blindness. Increased plasma concentrations of vitamin A occur but do not necessarily correlate with toxicity.
Affected organisms
  • Humans and other mammals
Pathways Not Available
理化性质
Properties
State solid
Experimental Properties
Property Value Source
melting point 63.5 °C PhysProp
water solubility 0.671 mg/L Not Available
logP 5.68 BIOBYTE (1995)
Predicted Properties
Property Value Source
water solubility 7.58e-03 g/l ALOGPS
logP 6.38 ALOGPS
logP 4.69 ChemAxon
logS -4.6 ALOGPS
pKa (strongest acidic) 16.44 ChemAxon
pKa (strongest basic) -2.2 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 1 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 20.23 ChemAxon
rotatable bond count 5 ChemAxon
refractivity 97.92 ChemAxon
polarizability 36.54 ChemAxon
药物相互作用
Drug Interaction
Acitretin Acitretin increases the risk of vitamin A toxicity. Avoid vitamin A supplementation while taking acitretin.
Bexarotene Bexarotene increases the risk of vitamin A toxicity. Avoid vitamin A supplementation while taking bexarotene.
Isotretinoin Isotretinoin increases the risk of vitamin A toxicity. Avoid vitamin A supplementation while taking isotretinoin.
Orlistat Orlistat may impair the absorption of vitamin A, a fat soluble vitamin. Oral vitamin A should be administered 2 hours prior to or post orlistat administration.
Tretinoin Tretinoin increases the risk of vitamin A toxicity. Avoid vitamin A supplementation while taking systemic tretinoin.
食物相互作用
Not Available

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