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曲安奈德 | 76-25-5

中文名称
曲安奈德
中文别名
确炎舒松;曲安缩松;醋酸曲安缩松;去炎松-A;9-氟-11b,21-二羟基-16a,17-[(1-甲基亚乙基)双(氧)]-孕甾-1,4-二烯-3,20-二酮;去炎舒松;确炎舒松-A
英文名称
triamcinolone acetonide
英文别名
(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one
曲安奈德化学式
CAS
76-25-5
化学式
C24H31FO6
mdl
MFCD00056834
分子量
434.505
InChiKey
YNDXUCZADRHECN-JNQJZLCISA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 熔点:
    274-278°C (dec.)
  • 比旋光度:
    D23 +109° (c = 0.75 in chloroform)
  • 沸点:
    576.9±50.0 °C(Predicted)
  • 密度:
    1.1517 (estimate)
  • 溶解度:
    几乎不溶于水,微溶于乙醇 (96%)。
  • 碰撞截面:
    197.1 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

计算性质

  • 辛醇/水分配系数(LogP):
    2.5
  • 重原子数:
    31
  • 可旋转键数:
    2
  • 环数:
    5.0
  • sp3杂化的碳原子比例:
    0.75
  • 拓扑面积:
    93.1
  • 氢给体数:
    2
  • 氢受体数:
    7

ADMET

毒理性
  • 在妊娠和哺乳期间的影响
哺乳期使用概要:因为没有关于口服或注射曲安奈德在哺乳期间使用的信息,可能更倾向于使用另一种药物,特别是在哺乳新生儿或早产儿时。然而,将曲安奈德作为鼻喷剂或局部注射,例如用于肌腱炎,不会预期对哺乳婴儿产生任何不良反应。专家意见认为,在哺乳期间可以使用吸入和口服皮质类固醇。局部注射,例如用于肌腱炎,不会预期对哺乳婴儿产生任何不良反应,但偶尔可能会导致暂时性的乳汁供应减少。另见曲安奈德,外用。 对哺乳婴儿的影响:没有报告任何皮质类固醇有影响。 对泌乳和母乳的影响:一位母亲正在哺乳她14个月大的婴儿,每天3到7次。她在肩部注射了5.7毫克倍他米松磷酸钠和醋酸混合物治疗滑囊炎,对泌乳没有影响。四周后,她继续在胸颈椎区域感到疼痛,并被诊断为神经敏感化。她在颈椎和胸椎硬脊膜外以及小面注射了80至120毫克的曲安奈德二醋酸酯。三天后,她注意到乳汁供应减少和喷射反射减弱,在接下来的5天内情况继续恶化。她开始使用频繁抽吸的吸奶器和多潘立酮作为催乳剂。她的乳汁在几天内慢慢增加,在注射后的21天停止多潘立酮时恢复正常。那时,她的血清催乳素水平升高。母亲乳汁供应的减少可能是由皮质类固醇注射引起的。也有报告称,在手腕注射一剂甲基强的松龙悬浮液会导致暂时性的泌乳停止。 一项对46名在34周前分娩的妇女的研究发现,如果在分娩前3到9天给予另一剂量的皮质类固醇(倍他米松,2次肌肉注射,每次11.4毫克,间隔24小时),会导致第二阶段泌乳延迟和产后10天内的平均乳汁量减少。如果婴儿在母亲接受皮质类固醇后不到3天或多于10天分娩,乳汁量不会受到影响。等效剂量的曲安奈德可能会有同样的效果。 一项对87名孕妇的研究发现,在怀孕期间给予上述剂量的倍他米松会导致孕期过早刺激乳糖分泌。尽管增加在统计学上是有意义的,但临床重要性似乎很小。等效剂量的曲安奈德可能会有同样的效果。 一位分娩后7个月的哺乳母亲在手背第一间隔区注射了40毫克曲安奈德,并加入了2毫升1%利多卡因治疗德奎尔万腱鞘炎。注射后24小时,患者报告乳汁量减少了90%,这是通过注射前后用吸奶器测量的。她继续吸奶,并开始服用葫芦巴以刺激泌乳。在1周内,她的乳汁供应增加了50%,在注射后1个月,她能够满足婴儿的哺乳需求。 一名患有特发性肉芽肿性乳腺炎的妇女在受影响的乳房的红斑区域注射了40毫克曲安奈德醋酸酯。她的乳汁产量从注射的左乳减少了。她原本能够用电动吸奶器在那边挤出60毫升,注射后只能挤出10毫升。受影响的乳房的乳汁供应在2周内恢复。未受影响的右乳的产量没有减少。
◉ Summary of Use during Lactation:Because no information is available on the use of oral or injectable triamcinolone during breastfeeding, an alternate drug may be preferred, especially while nursing a newborn or preterm infant. However, use of triamcinolone as a nasal spray or local injections, such as for tendinitis, would not be expected to cause any adverse effects in breastfed infants. Expert opinion considers inhaled and oral corticosteroids acceptable to use during breastfeeding. Local injections, such as for tendinitis, would not be expected to cause any adverse effects in breastfed infants, but might occasionally cause temporary loss of milk supply. See also Triamcinolone, Topical. ◉ Effects in Breastfed Infants:None reported with any corticosteroid. ◉ Effects on Lactation and Breastmilk:A mother was nursing her 14-month-old 3 to 7 times daily. She had 5.7 mg of betamethasone sodium phosphate and acetate mixture injected into her shoulder for bursitis with no effect on lactation. Four weeks later, she continued to have pain in her thoracic cervical regions and was diagnosed with neural sensitization. She had 80 to 120 mg of triamcinolone diacetate injected into her cervical and thoracic spine epidurally and into the facets. Three days later, she noticed a decrease in milk supply and a reduced ejection reflex which continued to worsen over the next 5 days. She began using a breast pump with frequent pumping and domperidone as a galactogogue. Her milk slowly increased over several days and was normal by 21 days after the injection when she stopped domperidone. At that time, her serum prolactin levels were elevated. The decrease in the mother's milk supply was possibly caused by the corticosteroid injections. A dose of depot methylprednisolone injected into the wrist has also been reported to cause temporary cessation of lactation. A study of 46 women who delivered an infant before 34 weeks of gestation found that a course of another corticosteroid (betamethasone, 2 intramuscular injections of 11.4 mg of betamethasone 24 hours apart) given between 3 and 9 days before delivery resulted in delayed lactogenesis II and lower average milk volumes during the 10 days after delivery. Milk volume was not affected if the infant was delivered less than 3 days or more than 10 days after the mother received the corticosteroid. An equivalent dosage regimen of triamcinolone might have the same effect. A study of 87 pregnant women found that betamethasone given as above during pregnancy caused a premature stimulation of lactose secretion during pregnancy. Although the increase was statistically significant, the clinical importance appears to be minimal. An equivalent dosage regimen of triamcinolone might have the same effect. A nursing mother who was 7 months postpartum had triamcinolone 40 mg injected into the first dorsal compartment of the wrist along with 2 mL of 1% lidocaine for de Quervain tenosynovitis. Twenty-four hours after the injection, the patient reported a 90% decrease in lactation as measured by breast pumping before and after the injection. She continued to pump her breasts and began taking fenugreek to stimulate lactation. Within 1 week, her milk supply increased by 50% and by 1 month after the injection, she was able to meet her infants breastfeeding needs. A woman with idiopathic granulomatous mastitis received an injection of 40 mg of triamcinolone acetonide into erythematous areas of the affected breast. Her milk production decreased from the injected left breast. She had originally been able to express 60 mL on that side with an electric breast pump, and after the injection she was only able to express 10 mL. Her milk supply on the affected side recovered over the course of 2 weeks. Production on the unaffected right breast did not decrease.
来源:Drugs and Lactation Database (LactMed)

安全信息

  • TSCA:
    Yes
  • 危险品标志:
    T
  • 安全说明:
    S45,S53
  • 危险类别码:
    R61
  • WGK Germany:
    3
  • 海关编码:
    2937229000
  • 危险品运输编号:
    NONH for all modes of transport
  • RTECS号:
    TU3920000

SDS

SDS:37e987f75f2dbebc077b941775f3acb6
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制备方法与用途

肾上腺皮质激素药:曲安奈德 概述

曲安奈德(Triamcinolone acetonide,TA)是一种肾上腺皮质激素药物。其制剂包括曲安奈德注射液和曲安奈德益康唑乳膏。它具有较强的抗炎和抗过敏作用,比氢化可的松强20~40倍。曲安奈德可用于治疗多种皮肤疾病、关节疼痛以及过敏性鼻炎,抑制各种炎症反应,并作为曲安西龙(Triamcinolone)的一种更有效的衍生物,其效力是强的松的八倍。

适应症与临床应用 适用范围

曲安奈德广泛应用于治疗过敏性皮炎、接触性皮炎、脂溢性皮炎、神经性皮炎、湿疹、银屑病(牛皮癣)、扁平苔藓等皮肤病及皮肤瘙痒症。它也可用于支气管哮喘、风湿性关节炎、急性扭伤、慢性腰腿痛、肩周炎、腱鞘炎、眼科炎症以及口腔黏膜充血、糜烂面、溃疡、肉芽肿性唇炎和口腔黏膜慢性感染性疾病等。

临床应用
  • 醋酸曲安奈德鼻喷雾剂可用于预防和治疗常年性、季节性和血管舒缩性过敏性鼻炎。
  • 关节内注射可消除炎症,缓解疼痛、肿胀及僵硬。
  • 肌肉注射后作用可持续2~3周。
化学性质与用途 物理化学性质

曲安奈德为白色或类白色结晶性粉末,无臭,味苦。它极微溶于水,微溶于乙醇,溶于氯仿,略溶于丙酮。

旋光度和吸收系数
  • 比旋度:+101°至+107°
  • 吸收系数为340~370,在239nm波长处测定吸光度。
化学用途

曲安奈德是肾上腺皮质激素类药物,用于治疗神经性皮炎、湿疹、牛皮癣、关节痛及支气管哮喘等病症。

安全性与贮运特性 毒性和危险性
  • 类别:有毒物品
  • 毒性分级:高毒
  • 急性毒性:
    • 皮下-大鼠 LD50: 13.1毫克/公斤
    • 腹腔-小鼠 LD50: 105 毫克/公斤
可燃性与灭火剂
  • 可燃,燃烧产生有毒氟化物烟雾。
  • 灭火剂:干粉、泡沫、沙土、二氧化碳、雾状水。
贮运特性
  • 库房需通风低温干燥
  • 与食品原料分开存放

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
    • 1
    • 2
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    曲安奈德 在 copper diacetate 作用下, 以 甲醇 为溶剂, 生成 9α-fluoro-11β-hydroxy-16α,17α-isopropylidenedioxy-3,20-dioxo-1,4-pregnadien-21-al
    参考文献:
    名称:
    Novel pregnanoic acid derivatives
    摘要:
    普鲁甲酸衍生物的一般结构式为##STR1## 其中是单键或双键;X为氢、氟或甲基;Y为氢、氟或氯;Z为β-羟甲亚甲基、β-酰氧甲亚甲基、β-氟甲亚甲基、β-氯甲亚甲基、羰基或亚甲基;R₁为氢、α-或β-位的甲基或亚甲基,R₂为氢、羟基或酰氧基,或R₁和R₂共同为烷基二氧基,U₁为卤素、含1-5个碳原子的卤代烷基或卤代苯基,是具有局部抗炎作用的有效成分。
    公开号:
    US04049804A1
  • 作为产物:
    描述:
    曲安西龙盐酸丙酮 作用下, 生成 曲安奈德
    参考文献:
    名称:
    16-Hydroxylated Steroids. VII.1 The Synthesis of the 16α-Hydroxy Derivatives of 2-Methyl Steroids2
    摘要:
    DOI:
    10.1021/ja01516a044
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文献信息

  • [EN] 3,5-DIAMINO-6-CHLORO-N-(N-(4-PHENYLBUTYL)CARBAMIMIDOYL) PYRAZINE-2- CARBOXAMIDE COMPOUNDS<br/>[FR] COMPOSÉS 3,5-DIAMINO -6-CHLORO-N-(N- (4-PHÉNYLBUTYL)CARBAMIMIDOYL) PYRAZINE-2-CARBOXAMIDE
    申请人:PARION SCIENCES INC
    公开号:WO2014099673A1
    公开(公告)日:2014-06-26
    The present invention relates compounds of the formula: or pharmaceutically acceptable salts thereof, useful as sodium channel blockers, as well as compositions containing the same, processes for the preparation of the same, and therapeutic methods of use therefore in promoting hydration of mucosal surfaces and the treatment of diseases including cystic fibrosis, chronic obstructive pulmonary disease, asthma, bronchiectasis, acute and chronic bronchitis, emphysema, and pneumonia.
    本发明涉及以下化合物的公式:或其药学上可接受的盐,用作钠通道阻滞剂,以及含有这些化合物的组合物,制备这些化合物的方法,以及在促进粘膜表面水合和治疗包括囊性纤维化、慢性阻塞性肺病、哮喘、支气管扩张、急性和慢性支气管炎、肺气肿和肺炎等疾病的治疗方法。
  • CHLORO-PYRAZINE CARBOXAMIDE DERIVATIVES WITH EPITHELIAL SODIUM CHANNEL BLOCKING ACTIVITY
    申请人:Parion Sciences, Inc.
    公开号:US20140171447A1
    公开(公告)日:2014-06-19
    This invention provides compounds of the formula I: and their pharmaceutically acceptable salts, useful as sodium channel blockers, compositions containing the same, therapeutic methods and uses for the same and processes for preparing the same.
    这项发明提供了式I的化合物及其药用盐,可用作钠通道阻滞剂,包含这些化合物的组合物,以及用于这些化合物的治疗方法和用途,以及制备这些化合物的方法。
  • Dual Pharmacophores - PDE4-Muscarinic Antagonistics
    申请人:Callahan James Francis
    公开号:US20090203657A1
    公开(公告)日:2009-08-13
    The present invention is directed to novel compounds of Formula (I) and pharmaceutically acceptable salts thereof, pharmaceutical compositions and their use as dual chromaphores having inhibitory activity against PDE4 and muscarinic acetylcholine receptors (mAChRs), and thus being useful for treating respiratory diseases.
    本发明涉及具有式(I)的新化合物及其药用盐,药物组合物及其用作对PDE4和肌胆碱受体(mAChRs)具有抑制活性的双色素,因此可用于治疗呼吸道疾病。
  • [EN] DUAL PHARMACOPHORES - PDE4-MUSCARINIC ANTAGONISTICS<br/>[FR] PHARMACOPHORES DUALS, ANTAGONISTES DES RÉCEPTEURS MUSCARINIQUES ET INHIBITEURS DE L'ACTIVITÉ PDE4
    申请人:GLAXO GROUP LTD
    公开号:WO2009100169A1
    公开(公告)日:2009-08-13
    The present invention is directed to novel compounds of Formula's (I) - (VI), and pharmaceutically acceptable salts thereof, pharmaceutical compositions and their use in therapy, for example as inhibitors of phosphodiesterase type IV (PDE4) and as antagonists of muscarinic acetylcholine receptors (mAChRs), in the treatment of and/or prophylaxis of respiratory diseases, including inflammatory and/or allergic diseases such as chronic obstructive pulmonary disease (COPD), asthma, rhinitis (e.g. allergic rhinitis), atopic dermatitis or psoriasis.
    本发明涉及式(I) - (VI)的新化合物,以及其药学上可接受的盐、药物组合物及其在治疗中的应用,例如作为磷酸二酯酶IV (PDE4)的抑制剂和肌碱乙酰胆碱受体 (mAChRs)的拮抗剂,用于治疗和/或预防呼吸道疾病,包括炎症性和/或过敏性疾病,如慢性阻塞性肺病(COPD)、哮喘、鼻炎(例如过敏性鼻炎)、特应性皮炎或银屑病。
  • [EN] QUINONE BASED NITRIC OXIDE DONATING COMPOUNDS<br/>[FR] COMPOSÉS DONNEURS D'OXYDE NITRIQUE À BASE DE QUINONE
    申请人:NICOX SA
    公开号:WO2013060673A1
    公开(公告)日:2013-05-02
    The present invention relates to nitric oxide donor compounds having a quinone based structure, to processes for their preparation and to their use in the treatment of pathological conditions where a deficit of NO plays an important role in their pathogenesis.
    本发明涉及具有喹诚基结构的一氧化氮供体化合物,涉及其制备方法以及它们在治疗病理状况中的应用,其中一氧化氮缺乏在它们的发病机制中起重要作用。
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表征谱图

  • 氢谱
    1HNMR
  • 质谱
    MS
  • 碳谱
    13CNMR
  • 红外
    IR
  • 拉曼
    Raman
hnmr
mass
cnmr
ir
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  • 峰位数据
  • 峰位匹配
  • 表征信息
Shift(ppm)
Intensity
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Assign
Shift(ppm)
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测试频率
样品用量
溶剂
溶剂用量
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